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 have you been finding dating?
There are a lot of ways to personalize this question based on the context of your date — How are you finding dating on OKCupid? What’s dating in Boulder been like for you? I know you recently separated – what’s dating after that been like? Regardless of the specifics, it’s a good way to begin to transition from general small talk to discussing relationships in general, and starting to get a sense of whether you two share similar values.
If dating hasn’t been going well — and who feels totally successful in dating? — it provides something to bond over; the easiest way to get a rapport with someone is to commiserate over a shared annoyance! More than that, though, their insights as to what they feel about dating and why are helpful. If they’re frustrated that everyone they date wants to be exclusive after two dates, and you’re looking for a serious monogamous relationship, that might be an early sign you aren’t a good fit. If they’re still going out with new people, it generally means they haven’t found what they’re looking for yet; this is a natural way to segue into talking about what that is for both of you and move into more direct communication about your wants and needs romantically.