Dear Dr. Frankie, I need some practice asking the right kind of questions on a lesbian date.
I don’t think I want to tell her right away what I’m looking for, and then distrust her when she tells me what she knows I want to hear. I think I want to ask her questions to get to know her and let her be herself.
Learning how to ask the right questions is something of an art form. While there are many things you’re probably curious about, you certainly don’t want to come across as intrusive or inappropriate, and you likely want to keep the conversation on the lighter side.
I often recommend that you avoid obviously heated topics such as politics and religion, or depressing topics such as previous relationship failures, family drama, and unresolved childhood issues.
And if you want a straightforward answer, that’s a great one – especially since sometimes people who discuss really personal topics on first dates can have poor boundaries and questionable judgment.
On the other hand, depending on what you want out of dating, it might be really important to you that your date aligns with you politically or that you share religious values before you figure out whether you want to see her again. It might be important to you to meet someone capable of self-awareness and emotional depth and to be able to demonstrate that early on. It also might be important to make sure you have compatible relationship styles – that you’re both monogamous or non-monogamous, that you’re both into BDSM, or that regardless of either of those things you both are open or not to marriage or kids.
If that’s you, then I suggest being honest, but not terribly specific. You can share that you’re looking for a long-term partner or a casual dating partner without talking about what timeline you’re on, what your ideal relationship would look like, or what you want to eat for breakfast together. You can share that you’re polyamorous without talking about how an ex-metamour recommended the place you’re having a date as a great first-date spot.
I recommend asking open-ended questions and noticing how your date responds. If you ask what she’s looking for, does she tell you what she wants to eat together for breakfast in five years, or does she more appropriately share the broad strokes but omit the details? Does she talk about what’s important to her in a partnership, or do you look up an hour later and realize the whole date has been processing around her ex? (No one has to show up fully healed, but processing a breakup on a first date is a good sign someone isn’t ready for a second.) What is she telling you both with the content of what she says, and how she says it?
When thinking about what you want to find out, the key is to be interested, but not intrusive. Give your date space to speak, and listen to what she tells you. If you want to know more, ask, “Tell me more.” If you notice yourself judging your date, arguing together, or not lining up on values that are important to you, then you’ve had a successful date because you’ve gotten information about whether you should have a second: you shouldn’t. If when you share what you’re looking for and so does she and you seem to line up, that’s a sign you might want to see each other again.
Overall, I think it’s less about asking the right questions and more about letting things unfold naturally and seeing where they lead. Thank you for asking and good luck.