Casual Dating: A How-To Guide
While many of us were raised on our parent’s views that anyone who wasn’t dating to marry was just out to use us, it’s a new and more sex-positive era; we can recognize that there are a lot of ways to connect with someone, and casual connections can be a great and fulfilling option for some of us based on our needs and experience. Maybe you’re focused on your career, or just got out of a serious relationship and want to take your time before diving back into the deep end; maybe you have kids and don’t want to bring someone serious into their life until they’re older. Maybe casual is just what you feel interested in right now; not everything has to lead to U-Hauling!
But what’s the difference between a casual dating relationship and just the early days of something more serious? And how do you manage intentionally casual connections in a way that makes everyone feel fulfilled and respected rather than leaving their feelings hurt? Here are a few tips on keeping casual healthy and fun.
Decide What You Look for from Casual Connections
Dating doesn’t always have to be about deep self-excavation, but it is useful to have some internal clarity about what you want out of any potential experience. It can be easy to base all of our casual dating aims (or even all dating aims) on what we don’t want: I don’t want something serious, I don’t want to get hurt, I don’t want to be tied down, etc. Instead, try focusing on what you do want: a fun, flirty connection that provides a break from the stress of your work-life; a sweet and sexy dynamic where you can take weekend trips together; someone who has a complementary set of sexual interests and likes watching crime documentaries with you, and is also happy to make plans just a few times a month.
While it’s not necessarily true that all lesbians are in the market for a wife, it might be helpful to both yourself and any potential dates to be able to explicate not only what you’re looking for in casual dating right now, but why. It’ll also help ground any later conversations you might have about what exactly the contours of your casual connection might look like if you’re both on board with the reasoning behind it.
Get Clear on What Casual (and Serious) Means for You
We often use the term ‘casual’ as if it’s a universally fixed term with a collectively agreed-upon definition — it isn’t! What feels eminently chill and low-key to you might feel like a hugely serious step to your date and vice versa. It’s helpful to identify what actions or life areas feel ‘serious’ to you in relationships, and which you feel you can engage in without associating the connection with a deep and permanent attachment — and, crucially, inviting your dates to share this information too. Some topics to think about might be:
Sleepovers after dates/sex — and making breakfast or hanging out the next day
Meeting family, friends, or children of your date
Certain sex acts – are there some you’d only want to do with a serious partner?
Sharing keys/keeping items at each others’ places
Amount of time spent together
Frequency of communication (calling, texting, Facetiming)
Emotional intimacy and emotional reliance on each other
Exclusivity
Each of these is very broad, which is why taking some time to think it through very honestly on your own is key. What are the hallmarks or milestones that, to you personally, serve as telltale signs that you’re getting serious about someone? How can you take control of your experiences by managing those things? For instance, if you know that meeting a partner’s friends or family is usually meaningful to you and something you place a lot of importance on, that might be something to specifically separate from casual dating, telling your dates something like “Thanks for inviting me to Kara’s party! I love hearing about your friends and getting updates – to me, joining in group hangouts with friends or family is something I associate with more serious relationships, so I’ll take a pass on plans with the whole group and wait for you to tell me all about it later.”
Some things might be barometers to keep an eye on across the board, regardless of your personal tendencies – for instance, if you’re spending every single day (or even every single weekend) together, or if your casual date is the first person you want to call for support or comfort when you’re feeling emotionally activated, that’s no longer a casual connection. While we sometimes like to throw up our hands and declare how helpless we were in the face of romantic feelings, the truth is that our feelings are intertwined with our actions and we have control over our actions — if you know someone is 100% not available for a serious relationship and that having sleepovers with them twice a week will mean you imagine them as your girlfriend, you have a choice to make sure you only see them twice a month and manage your own expectations.
First Date Conversation Starters
First dates are nerve-wracking, and for good reason — it’s a counterintuitive process where you meet up with someone who’s (usually) a total stranger, and both of you are hoping to some degree that it’ll lead to being more intimate than you are with almost anyone else. And that’s if it goes well, leaving aside concerns like whether you’re attracted to each other or like each other equal amounts.
A more manageable way to look at it is that a first date is a way for both you and your date to decide if you want to go on a second date. That means you’ll want to pay attention to whether you have fun, and also try to get to know the other person well enough to get a very broad idea of whether they’re the kind of person you’re looking for. Open-ended questions – ones that can’t be answered with a yes or no, or brief factual response – are great for inviting someone to open up and really connect, and showing that you care about really learning about them. To that end, here are some conversation topics that make it easy to get to know someone (and to share about yourself!) while also keeping the interaction fun and enjoyable for both of you.
How did you meet your best friend? (Tell me about them!)
You can learn a ton about new people from the important people and relationships in their lives — especially the close relationships we choose for ourselves rather than have determined by biology. It helps you get a sense of how they see and treat the most important people in their lives — they likely won’t treat a girlfriend the exact same as their best friends, but it will likely demonstrate some of their values about emotional intimacy.
In general, sharing about things that are emotionally significant to you is a good way for two people to get closer, but too often queer women interpret that to mean they should share about all their most intense trauma in great detail. Instead, ask to hear the backstory and details on a significant, positive part of someone’s inner world – and offer your own.
What do you like/dislike most about your job?
It’s standard to trade what each of you does for a living – in fact, you may have already done this before you even got to the date itself. But what someone does for a living doesn’t necessarily tell you anything about them. As single adults, we often don’t have anyone in our lives to talk to who wants to hear about our jobs, even though we spend most of our waking hours there; giving your date the opportunity to rhapsodize or rant about their work can feel really good to them, and also give you insight into their personality. If their favorite thing is getting to connect with new people on sales calls, you know they’re likely extroverted and outgoing with a lot of social skills; if they hate that their boss is so conflict-averse and passive-aggressive, that’s helpful information about how they like to interact with people.
As a kid, what did you want to do when you grew up? How does what you do now compare?
Learning about someone’s early years and childhood is such a key part of getting to know them — but for many of us, these are sensitive subjects, and our early childhood may have been marked by toxic family dynamics, trauma, or just stories we aren’t ready to share with a stranger. Asking questions like this gives your date an opening to talk about the full scope of their life, including their childhood, in a way that’s happy or at least neutral. It helps you get to know them better while giving them the agency and freedom to decide how personal they want to get, a very different experience than asking “how was your childhood?” It also gives you a chance to get a little bit of insight as to how they’re feeling about how their life is going — do they seem resigned when talking about their current lived experiences, or do they seem to feel aligned with their idealistic childhood values and have worked to make a life their childhood self would be proud of?
Do you believe in ____?
The question of whether astrology is real will divide the lesbian and bisexual community until the end of time. If you enjoy flirty bickering, it could be a great way to develop some banter; if zodiac signs are a topic you feel very strongly about one way or another, it could be a good way to quickly determine if you two share a worldview. Outside of astrology, there are tons of topics — ghosts! Psychics! Aliens! Bigfoot! Spontaneous combustion! — that are fun to hear people’s insights and experiences on.
Organized religions or the existence of God might be a bit heavy for a first date, but otherwise, these questions are often really energizing and fun ones to develop a rapport over without having to dredge up a lot of personal stories or share too much too soon. Maybe you’ll even have a few inside jokes about it for a second date!
How to Use Your Intuition in Dating
Deep down, you have an internal ‘super power’ that can help you navigate the dating process. It’s called your intuition.
Intuition is defined as “the ability to understand something immediately, without the need for conscious reasoning.” It can be a gut feeling, an instant knowing, a hunch, or an unexplainable ‘sense’ about something that turns out to be right.
For purposes of this article, let’s think of intuition as your internal guide or compass giving you a sense of whether or not a person or dating situation is healthy—or unhealthy—for you. This goes far beyond the first impression you have of someone. It taps into how you feel in their presence.
What is Intuition?
A psychology.com article says, “Intuition, like first impressions, serves the brain’s need to predict and prepare for what will happen next. First impressions are rapid, holistic assessments of people based on subtle perceptual cues and judgment of intent to help or harm. Both rely on automatic processes and, as rapid evaluation systems, both are subject to error, especially from biases we hold.”1
Your intuition uses all of your previous life history and experiences to try to help your brain make the right decision in the moment. It doesn’t even have to make logical sense.
Your brain doesn’t want you to be put in harmful situations, so it will try to avoid anything that can potentially harm you.
How Your Intuition ‘Speaks’ to You
Everyone has intuition, although some people may not feel connected to it. Some may appear to be more intuitive than others and may even come across as psychic. What matters is how your intuition speaks to YOU.
See if you resonate with any of these feelings:
You walk into a new place and your body tightens up; your muscles contract or you don’t feel safe—you have a gut feeling that something’s ‘off’
You meet someone new and you feel a dreadful sinking sensation in the pit of your stomach, or your muscles tighten up and you feel uncomfortable
You interact with someone new and you feel ice cold all over like something’s really wrong (and it’s not just the temperature in the room)
You walk into a new place and your body relaxes; you feel completely at peace, and you DO feel safe—you find yourself opening and expanding
You meet someone new and you feel an immediate sense of peace as if your nervous system is calmed by their presence—you find yourself leaning in towards them naturally
These are all intuitive feelings. The feelings can be subtle or strong (it’s different for everyone). But always pay attention to them, because it may be your intuition speaking to you.
How You Feel Around Your Date Says a Lot
Pay attention to how your body feels during the first few dates with someone—AND while you’re communicating with them to arrange the dates. I’m not just talking about physical attraction. How do you feel in their presence?
Do you feel ‘lit up’ (or enthusiastic) in their presence or shut down?
Do you feel open and expanded, or closed off and contracted?
Do you feel jittery? Nervous? Anxious? Does your chest feel tight? Does your body feel tense? If so, your intuition may be telling you, “No—this person isn’t healthy for me.”
Do you feel calm and at peace, as if your whole nervous system has been soothed?
Do you feel an instant recognition, as if you’ve known this person for a long time? If so, your intuition may be saying, “Yes—this person is healthy for me.”
If you’re searching for a long-term partner, how you feel in this person’s presence truly matters. If you feel like something’s off, trust that.
You might even have a conversation with your date about how they’re feeling and see how it unfolds.
(And if you’re super shy and have no idea how you feel, check out my “Shy Girls Guide to Dating.”)
It’s Not About Being Right or Certain All the Time
You may have a ‘feeling’ about someone that turns out to be wrong…and that’s okay. Sometimes that can be your own bias at play. Or maybe YOU have internal blocks that are getting in the way of your own dating process. (Click here to get coaching.)
Think of your intuition as an internal feeling that can help guide you in the right direction and steer you away from harm.
Test Your Intuition
After each date, reflect on how you felt with that person. Write your thoughts down in a notebook. What kind of behaviors and feelings did that person draw out of you? Did they make you feel crazy and insecure? Did they inspire you to want to show up as your best?
If you have “predictions” or intuitive flashes about the person, write them down and see if they turn out to be right or not.
You can also experiment and use your intuition to make decisions. For example, you might say, “I felt really good around that person—I’ll go on a second date with them (if they’re open to it).” Then see how the second date goes.
How to Bring Positive Energy to Any Group Setting (and Get the Most Out of It)
Meeting people, participating in groups, and putting yourself in new social situations is a great way to expand your horizons. Not only is it fun, but you can also learn a few things, build genuine connections, and potentially meet your new lesbian partner.
Many people have asked me for advice on how to show up in a group. It’s important to always be mindful of how you’re showing up—because your presence, attitude, and energy can have a strong effect on others (whether you realize it or not). Hopefully, you’ll have a positive effect!
Knowing how to conduct yourself in a group setting is not so much a skill as it is an awareness. Whether it’s online or in-person, always remember that you’re not the only one in the room. Other people are there. It’s not the “you” show. It’s about the group.
That said, here are 14 tips on how to show up in a group setting (and really, life in general).
Try to bring positive energy to the room. You’re probably in a group where others are trying to maintain positivity in their lives. So bring a positive outlook. Act like you’re happy to be there.
Smile, laugh, compliment others, and say how nice it is to see everyone. Be lighthearted. (If you truly don’t want to be there, then you can politely excuse yourself and leave.)
Come prepared with something you’d like to share. Have a few things in mind that you might want to bring up during the group event. For example, you could ask the group a question, or ask for opinions, advice, or recommendations. Tell a funny story, share an anecdote, or share a comment on a current event. Bring up a movie you recently watched, a great book or quote you read, something you ate, or a great restaurant you found. Don’t feel like you need to bring a whole dissertation. One simple share can go a long way.
Come ready to listen. Being in a group setting exposes you to new and diverse perspectives. You may hear something that sparks excitement in you to make a change. Or maybe something makes you curious to try a new activity. But none of this can happen if you’re not listening. Be present, and give the group your full attention.
Ask questions, then ask follow-up questions. Be curious about what others think. For example, if someone says they just found an amazing new hairstylist in your city, you could say, “I’m actually looking for a new stylist in that area. Do you mind sharing who you found?”
Beware of how much “space” you’re taking up. Don’t monopolize the time by talking the entire time. But also…don’t just sit there in silence and not contribute anything to the conversation. Your presence matters. But your presence isn’t the only one that matters. If you’re shy, challenge yourself to ask someone a question. If you’re an extrovert, challenge yourself to listen more.
Don’t treat a social setting like it’s group therapy. This isn’t the place to say inappropriate things, such as super-personal experiences that might be triggering to other people (like sexual assault). It’s also not the place to unload deep emotional wounds or trauma. Have some appropriate boundaries. Oversharing and over-focusing on all the bad shit that happened in your life can bring the whole group down. (It also makes people not want to engage with you.) Life is definitely hard—but much of how we experience things depends on our outlook. If you need therapy or counseling, I recommend an EFT counselor.
If you drink, don’t get drunk. Nobody wants to see you lose control of yourself. Keep yourself composed out of respect for the other people in the group (and yourself).
Don’t complain about things. This can be a tough one because you might not even realize you’re complaining. Instead of casually voicing to someone, “This coffee tastes gross”…try finding something to be grateful for. “I’m alive, I get to be in this amazing experience known as ‘life,’ and my partner might be in this room.”
Don’t nitpick, correct people, or argue about unimportant details. Your role in a social group setting is NOT to be a contentious lawyer arguing in court. You’re here to meet new people, share, listen, and connect.
Don’t make judgments. Everybody has flaws. Everybody’s imperfect. And everyone’s at different stages in life with different levels of awareness. What you’re judging is probably something you’ve done in the past in some way, shape, or form. So try to have compassion instead of judgment.
Don’t tell people how they should act or behave, or give unsolicited advice. Advice is best received when someone asks for it and genuinely wants to receive it. If it’s not requested, it usually falls on deaf ears. Plus, unsolicited advice can be annoying (and not even applicable).
Be careful with sarcasm and teasing. It can easily get lost in translation, especially on Zoom. Sarcasm can be insulting. It hinders the group’s ability to make connections with each other and inadvertently causes discomfort in others.
How to Handle a Trigger While Dating (or in a Relationship)
Sex can be a more difficult topic to talk openly about than others for a lot of reasons, but having an overall baseline of comfort and security in discussing personal topics can help make it as approachable as possible.
Think about how your communication works overall in the relationship – do you regularly discuss your likes and dislikes, or why you feel the way you do about things? Are you both comfortable sharing (and hearing) a strong preference? Does your relationship allow for saying things like “actually, I don’t think I feel up to cooking tonight, can we change plans?” or “I think I want to change careers”? Working to make sure you both feel free to share anything with each other without fear of backlash or judgment will go a long way in making your communication about sex healthy as well — and empowering you both to step out of your sexual comfort zone.
The hardest part is understanding that your reaction is largely about you—not the other person. Your trigger is about you, your feelings, your patterns, your reaction, your unconscious tendencies, your automatic defense mechanism kicking in.
Triggers can come from a deeply held or unconscious belief you have. They can have a lot to do with your early childhood experiences and anything else that influenced you subconsciously.
For example, if you were bullied in school and the bullies made certain comments about your appearance (or a specific part of your body), you may get triggered whenever you hear similar comments being made about you or someone else.
The important thing is to understand that you can (and should) take responsibility for how you’re reacting. Taking responsibility gives you your power back—because you can choose your response instead of blindly reacting to the trigger.
See the Trigger as an Opportunity for You to Grow
One of the most empowering ways to look at life is to believe life is happening “for” you, not “to” you.
No matter what’s going on—on a date or anywhere else—try to see it as a gift, a lesson, or an opportunity to grow and increase your awareness. This reframe allows you to view all your dating experiences through a more empowering lens.
Catch Yourself Being Triggered in the Present Moment
A trigger is unconscious, so most people don’t realize when it’s happening.
Your job is simply to develop more awareness. Your goal is to catch yourself in the moment before you react and say something you’ll regret. You can take a deep breath (or three deep breaths) to collect yourself before you respond. Put space between the “stimulus” and the “response.”
I know, it’s easier said than done. But awareness and mindfulness are key.
For example, let’s say your date uses a certain word or phrase in a way that irritates you. Or maybe your partner has a habit of saying a certain phrase, or they breathe funny, or they make a weird sound and it grates on your nerves. They don’t realize they’re doing it. And you don’t realize you’re being triggered by it.
You’ve had a rough day. You meet with your date, and she says the phrase. And you just lose your sh#t. You can’t handle it. Not today.
Depending on how much awareness you have, you’ll either react emotionally and unconsciously and go off on your date (or partner)…or you’ll take responsibility for your trigger and you’ll communicate what’s going on with you.
“[Name], I had a really rough day today and for some reason, I’m feeling SO triggered by your use of the word, ____.”
Be mindful of your tone of voice. This kind of admission can either lead to a good conversation with your date that brings you closer. Or it can lead to your date getting defensive and getting triggered herself.
If you come from an authentic, vulnerable place, you’ll have a greater chance of having a productive conversation from it. (See my blog post on “Fierce Conversations” for help with this.) The goal for this kind of conversation is to get everything out in the open and find a way to say things that are difficult to say—like sharing your thoughts without labeling them as truth and without judging the other person’s opinions.
If It’s Really Intense…
If they say something way out of line and you feel like you have to get away immediately, you can tell them something like:
“I’m really upset right now. I’m going to say something I’ll regret. So I need like 15 minutes to an hour alone to think about this.”
Or, “I’m SO upset by what you just said. I’m not even sure how to respond right now. I feel so frustrated and need to go for a jog. I’ll be back, and we can talk about this later.”
Let them know that you’ll be back and you can discuss it then. (Don’t just leave them hanging.)
And make sure you actually DO discuss the trigger—especially if you’re with a long-term partner. This isn’t something you want to sweep under the rug. Otherwise, resentments can build up.
Dig Deep into the Trigger on Your Own Time
How to Talk About Sex
We all know we’re supposed to communicate if we want a healthy and satisfying sex life with a partner, and that talking about what you both want is the key to getting it. But we all grew up with different levels of comfort with our own sexuality and sharing it with others – talking about our own sexual desires, in particular, can feel terrifying for some people who grew up with shame or discomfort around their own sexuality, or in homes where any discussion of sexuality at all was taboo. Here’s how to start navigating talking about sex with a partner when you have different levels of comfort with the topic.
Identify What Makes Discussions Most Comfortable For You
Lots of couples use specific strategies for discussions that might be emotionally charged or heated; sex as a sensitive topic is no different. Think about what sets you up for success when it comes to good communication – is it talking face to face so you can see the other person’s nonverbal communication? Or communicating in writing so you can think carefully about what you want to say?
Similarly, you can talk with your partner about what would make them feel most confident going into sensitive discussions, especially if they’re someone with a lower level of comfort than you when it comes to talking about sex. Would they feel reassured knowing that they could end a conversation at any time if they get uncomfortable, no questions asked? Or using (or avoiding) specific language or names of body parts?
Many people recommend talking about sex in a different setting than sex itself – for good reason. Maybe you’ve had the experience of settling into bed immediately after sex that you thought was great only to have your partner say “you know, I wish you would do X more often.” It’s easy to feel vulnerable and sensitive in that context, even when you know you do in fact want to hear your partner’s feedback. Save discussions of your sex life for a neutral, calm setting outside the bedroom, at a time when you and your partner are feeling stable and connected.
Commit to Mutual Vulnerability
One difficulty in situations where there’s a differential in how experienced or comfortable someone is with sex is that there are often two layers of discomfort: you might feel embarrassed or self-conscious talking about sex, and then you also feel embarrassed or ashamed of feeling that way in the first place.
If this describes you or a partner, it’s helpful to commit to understanding this as a shared dialogue that’s vulnerable for both of you. Although people may have different levels of experience with sex as a whole, you both have the same amount of (in)experience when it comes to sex with each other, and everyone has insecurities, fears, or points of confusion to unpack.
It’s helpful if everyone involved can be upfront about the things they’re working through or questions they have (in a way that isn’t blaming or pointing fingers) to stay on track with the fact that communicating about your sex life (and making it easy for the other person to share too) is a collaborative process, not something just one of you ever needs to work on.
Stay Concrete Rather Than Open-Ended
When it comes to communicating about sex and relationships, we’re often advised to ask questions like “what do you like?” or “what do you want?” These are key things to know, but can also be really challenging questions to answer fluidly in the moment – kind of like being asked “why should we hire you?” in a job interview. If you have any discomfort or self-consciousness around sex, trying to spell out your desires — or admitting that you aren’t sure about them — can be excruciating.
Instead of posing high-stakes open-ended questions, see what it feels like to offer options — almost like an optometrist asking if 1 or 2 is clearer. “Is role-playing or having a hotel room affair a hotter fantasy to you?” “If I want to initiate sex, would you rather I ask out loud or try kissing you?” It can help things feel less like a quiz or interview if you can offer up how you feel as well – “I know I usually like to cuddle right after sex because it makes me feel closer to you. Do you like cuddling and talking after, or would you rather have a glass of water and rest for a minute?”
This technique can be especially useful when trying to communicate during sex itself, which can be a time when emotions are running high and it can feel like direct communication might break the mood or ruin the moment. Instead of asking “do you like that?” which can feel like it’s impossible to say no to, you can try asking “do you want me to keep doing this, or do X instead?” Or even something like “Do you want this softer, harder, or to switch to something else?”
Focus on Security and Unconditional Acceptance
Coming Out Later in Life
Conversations about coming out are so often conflated with youth, adolescence, or even childhood. As happy as we collectively are to see more and more youth able to name their identities and live openly, it can be alienating for those of us who recognize ourselves to be on a similar journey of self-discovery in adulthood. We may feel we’re at an age where we’re already meant to have figured everything out – or that lesbian or bisexual life is centered entirely around youth culture, and that there’s no point in coming out if our day to day life looks more like 10 am Zoom meetings and blood pressure meds than clubbing or college study dates. Despite that cultural narrative, the reality is that many of us can and do come out later in life – even into our 70s and 80s – to find fulfilling community, partnerships, and sense of self. If that feels like what you need, here are some of my thoughts on where to start.
(Compassionately) Let Go of Your Assumptions
In order to get to the level of self-awareness and self-acceptance you’re at now, you likely had to let go of a lot of long-held assumptions – that if you were gay you would already know, that everyone secretly felt the way you did, that NO one else felt the way you did, or that your life would be over if you ever came out. It’s great to have worked on challenging those somewhat, and to be in a place of working on noticing the ways in which real life is less black and white than those assumptions would presume.
Even now, though, there’s a good chance you’re (unintentionally) adopting a whole new set of assumptions, ones that run through your mind in moments of fear, anxiety, loneliness or shame. They might sound like any of these:
● No one will ever believe I’m really gay.
● I’ll never be accepted in queer community if they knew I was married to a man.
● Everyone else knows how to date except me; I have no idea what I’m doing.
● If I meet another lesbian in real life, she’ll be able to tell right away I don’t fit in.
● No one will want to date someone who has no experience with other women at this age.
● There are so many identities and categories; I’ll never be able to get it right.
● Everyone else came out twenty years ago; I’m the only one playing catch up.
● I’d be laughed out of the bed of anyone I tried to sleep with because I have no idea how to have lesbian sex.
These are also very black-and-white assumptions, and you’ll feel a lot less shame and anxiety in this part of your life if you can work on (compassionately) checking yourself about them. When you notice these thoughts come up or inform your behavior, you can practice gently asking yourself “am I sure that’s true?” Do I really think I’m the only person on earth who’s in this position? Do I really think everyone else is just a dating pro? Is it possible things aren’t quite so extreme? Get into the habit of gently correcting these thoughts: “It’s true I’m not as experienced with lesbian sex as some people might be; there was also a time when I didn’t know anything about sex at all, and I learned. Everyone has something to learn, and I’m still a caring, attentive partner who brings a lot to the table.”
Focus on Community, Not Just Dating
Entering the dating pool as someone who came out later in life can be intimidating; in some ways, finding queer friends can feel almost even scarier. Making real friends in adulthood is hard for anyone, and it may feel like it’s not worth the risk. But queer communities of friends are one of the most affirming and joyous parts of being out, and getting to know other gay women will help you check some of your assumptions — you may find that everyone else doesn’t have it as figured out as you imagine they do, and you have more in common than you thought.
A special characteristic of queer communities is that the commonalities in our experiences bring us into relationship with each other in unique and unexpected ways – you may feel like you have more to share with a 22-year-old who also just came out and who you meet through a local community group than the straight friends you’ve known all your life. If you’re a cis woman, you may find trans women in your community you feel a lot of connection with – they also frequently have their lesbianism called into question. If you’re a lesbian who came out later in life, you may find more shared ground with bisexual women than you expected – they also have their identity invalidated if they haven’t always dated women. (Also, while community is key outside of dating, there’s no more classic gay meet-cute than meeting as friends first.)
Ok, But What About Dating?
Even people who have been out for years find gay dating challenging (for that matter, so do straight people. Dating is hard!). Any feelings of inadequacy or insecurity can feel magnified in the vulnerability of wanting to find a partner, and you might imagine that everyone else knows things or has experience you don’t.
How to Date a Trans Person: A Guide for Cis People
So you’re cis – i.e., not trans – and you have an upcoming first date with a trans woman. Or maybe you’ve been going out with someone for a few weeks and she just came out to you as trans. Or you keep seeing hotties with they/them pronouns in their bios and you want to know what you need to know before you slide into their DMs. Here, for fellow cis women, is an extremely general introduction to how to date trans people.
Remember: I’m a cis woman and not an expert on transness. As cis people, it’s our job to educate ourselves and also listen when trans people share their lived experiences with us. The expert on how to date an individual trans person is the individual trans person you want to date. That said, here, for fellow cis women, is what to know when you’re starting to date trans people.
What’s The First Thing I Need to Know About Dating a Trans Person?
Seems obvious, but the first step to being a cis person who dates trans people is to not be an asshole. How do you not be an asshole? Here are some suggestions:
Share your pronouns when you introduce yourself, and then ask for theirs. If you mess up down the line, it happens. Apologize, correct yourself, and don’t do it again.
Treat your date like your date. How would you act on a date with a cis person? That’s how you should act on a date with a trans person. Be flirty, be respectful, be interested. Don’t ask about their gender or sexual identity or medical history, just like you wouldn’t ask a cis person.
Remember that trans women are women and trans men are men. If you’re a cis woman on a date with a trans woman, you are two women on a date.
Learn on your own. For instance, if you’re going on a date with a trans person and you don’t know why saying “transgendered” instead of “transgender” is offensive, you should educate yourself so your date doesn’t have to.
What If I’m Not Sure If My Date Is Trans?
Trans people, especially trans women, face a disproportionately high rate of violence. Some trans people are very public with their transness, whether by choice or by necessity, while others aren’t. If you’re not sure whether your date is trans, and your date hasn’t told you, then you can assume she’ll tell you in her own time if and when you reach that level of trust.
Okay, My Date Just Told Me She’s Trans and Now I’m in the Bathroom Reading This to Make Sure I Say the Right Thing
Take a deep breath. Your date trusted you with something personal, and like any other moment of trust in any relationship, there’s no one thing you can say that will be “the right thing.” Respond with gratitude and openness. You can ask if there’s anything specific she wants you to know about that right now, or you can let the conversation flow. Do not ask about her genitalia unless she brings it up first. (See: don’t be an asshole.) Just keep getting to know each other.
That Went Really Well, But I’m Just Not Feeling It
There are lots of reasons to keep getting to know someone and lots of reasons to decide to go your separate ways. Check-in with yourself: are you not interested in continuing to get to know your date because she’s trans? If the answer is yes, you have some work to do on internalized transphobia. If the answer is that it is genuinely not a good match, then go your separate ways.
That Went Really Well, And Now We’re Talking About Hooking Up
Congratulations! This part’s the easy part. Why? Because you already know that you should never make assumptions about what anyone likes in bed. Like you would for any sex date, talk about your safer sexual practices in advance. You can share a few things you’d like to do, and ask what she’d like to do. Listen and figure out where you overlap. There are lots of ways to have lesbian sex with a trans woman. If you want to learn more, Mira Bellwether’s Fucking Trans Women zine is required reading for anyone having sex with trans women.
That Went Really Well, And Now We’re Dating
As you become bigger parts of each other’s lives, you might come across instances where you notice that you have different privileges than your trans partner. This can come up in small ways, like needing to find a gender-neutral bathroom instead of a gendered one. Or it can come up in bigger ways, like needing to leave somewhere that feels unsafe. In those moments, defer to them and their experiences.
Building a long-term relationship is full of joy and challenges, regardless of gender. Being respectful, asking questions instead of making assumptions, and practicing vulnerability and openness is important no matter what.
How to Think About and Engage with Fantasies
Virtually everyone has sexual and romantic fantasies, from idle passing thoughts to powerful, detailed narratives that form a meaningful part of our sexual life. Fantasies also look different for everyone, meaning there’s no “wrong” way to have them. Imagination and daydreaming are how we work through lots of important or complex ideas, from our eventual dream house to what our career might look like — sex is no different. How do you make sense of what fantasies come up for you, and what role (if any) should they play in your partnered sex life? Here are some places to start thinking through your fantasies and how you might want to engage with them.
What does having a fantasy mean?
Fantasies can be drawn from books, TV, porn, our real experiences, experiences we wish we could have, even sexual possibilities that make us anxious (nervousness can feel similar to excitement!). Our fantasies often include things that push some kind of button for us, positive or negative; they might be based on things that have an emotional charge for us as well, which is why go-to fantasies might still be drawn from the first erotic thing we were exposed to as teens even when we’re well into adulthood, or memories of otherwise mediocre sex with a partner we were head over heels with. A fantasy can be a brief idea of a moment or a detailed, lush fully imagined dream world; they can feature you as a real person with your real sexual partner, fantasy characters or elements, or even only imaginary characters that don’t represent you at all – like watching a movie.
Although we think of fantasies as revealing what we want sexually, it can be a little more complicated than that – a fantasy could be an extreme or fantastical version of something we’re interested in, something we find it titillating to think about but aren’t sure if we would like in real life, or even something that we know we don’t want to try but turns us on to think about because it’s taboo. Our fantasies can be useful for learning about what we want in bed, but aren’t a printout of our exact desires – it’s normal and healthy to fantasize about things you know you don’t want in real life. At the same time, particularly powerful or recurring fantasies can also serve as a waypost for sexual experiences that might be fulfilling in our real lives.
Why share fantasies?
It’s fun to keep fantasies to yourself to rifle through like a private multimedia library; it can also be hot and intimate in some contexts to share them with others. Trading fantasies with others online can be a fun digital dating experience, especially in a pandemic where distanced options might feel safer. Much like fantasies themselves, digital chatting doesn’t have to get bogged down in the logistical details of the real world – you can stay anonymous and so can your fantasies.
Alternatively, you might be in a committed partnership and consider whether you and your partner want to share what you fantasize about with each other. Much like any other kind of intentional vulnerability, sharing something so personal and charged can create new trust and intimacy, which can translate into your sex life regardless of whether you choose to act on any fantasies or not. Talking about your fantasy life can be a way of helping your partner get to know what you like and how you see the world sexually – even if you don’t want to act out a certain fantasy beat for beat, understanding what turns you on about it could help your partner bring something new and special to your sex life.
That said, it shouldn’t be a requirement or expectation that fantasies be shared – people maintain their own sexual and psychological selfhood even when they’re in relationships, and demanding to know everything about someone’s fantasy life (or porn habits, or previous partners) can be a sign of harmful controlling behavior.
What do you and your partner want to share?
Fantasies can be something that stays in our private dream world, and some of them we might prefer to keep that way – we might have fantasies that are impossible in real life or that we don’t know if we would actually like, or we might prefer to keep something in our heads where we can never be disappointed by imperfect partners or sudden back pain.
Even in that case, though, there might be the seed of something we want to bring into our real lives – maybe we can’t really meet Marlene Dietrich at a black tie gala and be swept away into a life of glamor and five-star hotel suite trysts, but you could propose an anniversary weekend where your partner takes you to dinner and dancing in a tux and then sweeps you away to the penthouse suite while old movies play on the TV.
How to Repair Relationships After Conflict, Rupture or Disconnection
We often work hard on our conflict skills when we’re trying to improve our relationships – communicating directly, fighting fair, and listening openly. These are key steps, and often something we have to learn on our own if it isn’t modeled for us when we’re young.
After the conflict, though, is another step many of us have never seen done consistently and well: repairing the rupture. No matter how well a conflict is handled, it’s hard to move on and learn from the hurt without an active effort at reconnecting — here’s what to keep in mind for repairing successfully.
Set Your Intention for Repair, Not Being Right
Repair has different goals than conflict itself; it’s not about winning, it’s about reorienting so you and your partner can get back on the same team. It’s hard for repair to be authentic if either you or your partner are making reconnection conditional upon being right. Practice reminding yourself that you’re not talking about the hot button issue itself right now, but what each of you need to feel secure when it comes to addressing it. If you find either of you are getting caught up in rehashing the details of your disagreement or getting sidetracked into other issues, be ready to name that that’s happening and guide the conversation back to your goal of repair.
Take the Step of Initiating (or Receiving) Repair
We’re often feeling defensive, hurt and on edge after a fight; it can feel uncomfortably like swallowing your pride to initiate a conversation about repair, like you’re signaling weakness or admitting you’re wrong. It’s vulnerable! That fear of vulnerability is what can cause normal arguments to calcify into long term relationship challenges.
It’s much easier (or feels that way!) to let things slowly return to baseline — to struggle through a day of awkwardness with each other or passively avoid your partner until it feels like the issue is forgotten. But to genuinely move through and beyond conflict in a way that deepens your relationship, at least one partner has to take the step of saying out loud “Can we talk about what happened yesterday? I want to make sure we can resolve what came up there,” or “I know that fight this morning was hard, I won’t feel good without making it right – when can we talk?”
For this to work, it’s also key to be open to receiving repair — responding to the offer of repair in the good faith that it’s meant, rather than sulking, making repair conditional upon an ultimatum, or continuing the fight: “Oh, so now you want to hear what I have to say?” Being open to repair doesn’t mean you’re giving up the values or experiences that mattered to you during the conflict; it means you’re open to focusing on your relationship beyond that conflict so that you can learn and grow from the rupture.
Identify What Would Create Safety and Connection
If confirming who was “right” about your conflict isn’t the point, then what is? Fights (especially the intense ones) often arise when something makes one or both of you feel insecure or unsafe, either due to a specific trigger around past trauma or something that signals to us based on the attachment patterns we know that our relationship is threatened. The ensuing fight itself often creates new opportunities for those buttons to be pushed, and leaves us feeling deeply disconnected from our partners. For repair to be successful, we need to be able to talk about what would make each person feel both safe and connected again.
This could mean unpacking some of why the original fight was so charged for you, or talking about how you fight. You might be able to identify that the car is a loaded space for you because you associate it with fights on long family road trips as a child, and ask your partner to bring up difficult topics in a different environment, when you aren’t driving. Or your partner might share that your leaving the room when you’re fighting makes them feel abandoned and like your relationship is in danger, and that they’d come from a more secure place if you could announce explicitly that you want to cool down and process on your own and give them a time when you’ll be back to talk more. You don’t have to fold and agree that you’ll come to your partner’s holiday party, but you can listen to them explain that they got so upset when you said you couldn’t make it because they felt hidden and like you didn’t want to claim them publicly, a relationship trigger for them based on past experiences — and you can resolve to keep that in mind and speak directly to that fear in the future.