First dates are rarely anyone’s favorite part of dating — they can be awkward, tedious, and hard to schedule — but they’re part of the package if you ever want to progress to a transcendent third date or blissful first six months of dating.
Many of my clients ask me how they can make first dates more constructive and worthwhile. They want to know what kinds of questions they can ask to be confident that someone is realistically compatible. That way, they’re not wasting time on four more dates before realizing it’s not a good fit.
Here’s my recommendation for first date questions to ask that are fun, connective, and also help you evaluate your date’s compatibility:
1. What Are You Looking For?
A first date is supposed to be fun, but it’s also something of a fact-finding mission. In addition to seeing if you and this person have chemistry or feel attracted to each other, you want to find out if you could realistically make something work romantically or sexually.
Part of this is finding out if you want the same thing, whether that’s a serious relationship, marriage and kids, or a casual-but-consistent sexual partner.
If you learn you aren’t on the same page, you’ve saved yourself the time and heartbreak of getting too invested in someone who is incompatible.
2. What Have You Read or Watched Lately?
This question bridges the gap between idle small talk and deeper get-to-know-you questions.
Asking about someone’s media diet helps demonstrate your interest and warmth, but also helps you learn more about them as a person.
Learning that someone is up to their neck in the latest reality TV series is helpful characterizing information (and might help you find common interests if you’re watching the same show!). This is a very different vibe than someone who’s doing an annual rewatch of Angels in America.
3. What Do You Think About The L Word or Chappell Roan or Portrait of a Lady on Fire?
We all know there are many different kinds of lesbians, from jock rugby players to quiet board game nerds to political firebrands.
While these are, of course, oversimplifications, and real people have nuanced personalities and beliefs, it can be helpful to quickly locate someone else in the universe of lesbian values and culture.
This doesn’t mean they have to have exactly the same opinions as you — maybe you still mostly keep your Indigo Girls CDs in rotation, but you’re happy to join your date in a duet of Red Wine Supernova for karaoke.
But scoping out how some of the biggest names in queer pop culture land with your date might help you triangulate where you land relative to each other in the shifting sands of community.
4. When Did You Know You Were Gay?
Conversations about identity can be tricky on lesbian first dates. On the one hand, it can be very personal; on the other, it’s a major piece of shared experience that makes sense to bond over.
It can be useful to find overlaps in your experiences and discover shared common ground.
For example, the memory of a first schoolgirl crush can feel universal at times.
It can also be constructive to find where your experiences differ. Maybe you’ve been out since high school, but your date has only discovered she’s gay as an adult or in the midst of ending her marriage to a man.
These topics can feel vulnerable, so tread lightly, but asking compassionate, curious questions and listening deeply to someone else’s experiences with identity and self-knowledge can build intimacy quickly.
5. Are You a Top or a Bottom?
Sexual roles like top/bottom aren’t a necessary part of gay culture or sexual lifestyles for all lesbians, and depending on your dating goals, it’s possible that sex isn’t your priority to figure out on a first date.
But for many of us, finding someone with a compatible sexual role is a key component of a happy future together; everyone knows someone who met the ostensible love of their life only to find that they were both bottoms.
If you’re uncomfortable broaching this topic directly, it’s easy to do with some lightness and humor — “Ooh, thank you for ordering for me, so assertive! Are you a top?”
6. Who Was Your First Crush or Root?
A lesbian root is a formative experience crushing on a woman for the first time. It’s usually in fiction. Xena the Warrior Princess is a popular one for elder Millennials and Gen Xers.
Many of us have charged memories of a first person, character, or celebrity who made us feel an intense flood of feelings that we became aware our straight peers didn’t share. Whether it was Shego in “Kim Possible” or Linda Hamilton in “Terminator 2,” queer women often have strong feelings about these crushes.
“I remember being in middle school, and Gillian Anderson giving me confused feelings. She still gives me feelings, just not confused ones.” -Anonymous
Asking someone to tell you about their “root” can be a sweet way to get to know each other, as it hearkens back to a time when everyone was younger and less sure of themselves and their identity — but it can also speak in some ways to their current “type” and why they’re attracted to certain people.
7. What Kind of Relationship Do You Have With Your Ex(es)?
Exes can be a fraught topic on a first date, but it can also be eye-opening. For some (many) of us, our exes are our best friends, for better or for worse — we’ve remained close with them or forged new friendships with them, and they remain a big part of our lives.
In other cases, and sometimes even for the same person, there are exes with whom we have an incredibly acrimonious relationship and cannot be in contact with them in any way, or even in the same city.
If someone only has acrimonious relationships with all their exes, or if they consistently describe all their exes as having been “crazy” or in the wrong, it may be a red flag about their conduct in relationships.
Choose Your Words Carefully
It can be helpful to bring up a mix of serious and casual topics on a first date to scope out whether you and that person are aligned across the board. It’s also a good idea to try to find red flags early. If you’re someone who tends to feel very jealous and threatened, and your date has three best friends that they’ve previously dated, it may spell trouble down the line.
As a lesbian dating coach, I recommend that singles dive deep on that date and get beyond idle chitchat to truly find out if there’s enough compatibility to merit a second date.
