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.

Make a Plan to Reinforce Boundaries


No matter how carefully you plan your affairs of the heart and set your intentions about casual vs. serious behavior, even the best-laid plans oft go astray. When you (inevitably, to some degree) find yourself or your date slipping a bit — texting every day when you agreed not to, or leaving a change of clothes at your place just in case they sleep through their alarm and have to rush to work after a sleepover — you’re likely not going to feel super motivated to address it. It’s an uncomfortable conversation, and likely the reason you’re making those “exceptions” is because they feel good! Of course, you won’t really want to put a stop to it – that’s why it’s helpful to make a plan for how you might address it ahead of time, like making a plan for how you’re going to get home from the bar before you start drinking.

Set yourself up for success by thinking through a simple script to use if a situation like this comes up. That way you’ll have it ready to use and reduce the risk of handling it in a way you might regret, like suddenly distancing yourself or ghosting them, or pretending you don’t notice what’s happening and getting yourself in too deep. It doesn’t have to be complicated – even “Hey, thanks for bringing over tacos last night, it was great to see you. I wanted to check in – we had talked about making plans once every two weeks or so, and we’ve been seeing each other a lot more than that recently. How are you feeling about that/do you feel okay about that/do you feel like anything is changing we should talk about?” Make open-ended space without expectations or demands for both of you to voice how you’re feeling, what you need, and what your ideal outcome(s) for the situation is.

It doesn’t necessarily have to be accusatory or difficult, or even mean that you change anything! It’s totally possible that opening up a conversation like this will end in you agreeing you want to see each other more seriously, or that your thoughts around what boundaries you need have shifted. More communication is always good, even (or especially) in casual dynamics!

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