The Best Questions To Ask Her On A Date

I recently worked up the courage to ask a woman I work without a date, and she said yes! I’m really excited, but I’m also super nervous. What kind of questions should I ask her? What should I say? Help!

Geoff K.

Well, well, well Geoff, you’ve gotten an adult (I hope) female woman human specimen being person to agree to go on a date with you! Congratulations!

Normally I’d spend this part of the letter mocking you, but I don’t want to sh*t all over your very apparent excitement and anticipation, so I won’t! You done good buddy.

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But oh no! Now you actually have to go on a date with her! Can you imagine? The horror of conversation, of empty pauses and breaks filled only with awkward chewing and hastily broken off eye contact.

The feeling of warm liquid sh*t running down your leg as you fail to think of something, even a single thing to say to the woman in front of you, and your bowels involuntarily release as your brain prepares you for imminent death.

The humiliation of the busboy and the maître ‘d helping you clean it up and pretending that it’s not a big deal, and I’m sure she’ll still be there when we exit the bathroom sir, yes sir it wasn’t that noticeable, you played it off really well sir, may I suggest you leave a larger than normal tip sir, thank you sir, you are most kind.

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Remember that part where I told you I wasn’t going to make fun of you? I lied.

But that doesn’t mean I’m not going to help you! Double negatives! F*ck!

Anyway, you’re worried about what you’re going to say to her, which is understandable, but a bit misguided.

Misguided? Why?

Because she’s a person. You know people in your life. You’ve talked to people in your life before. Talk to her like she’s a person.

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You’re going to be hanging out with her in a setting that’s not work, so that’s going to feel new, and maybe a bit scary. But it’s not. It’s just an opportunity to get to know her for who she is outside of work.

I don’t know where you work, but it might be hard for her to fully let loose and be herself while she’s there. So give her the opportunity to while you’re on her date.

Ask her what she’s interested in. What gets her excited (in life, not in bed you f*ck, wait a while to pop that question). What she does when she’s outside of work. What kind of art she’s into in terms of movies, books, tv, whatever.

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Now is your opportunity to get to know what kind of a person she is. I’m sure you have an ideal version of who she really is built up in your head, but that’s going to come crashing down sooner rather than later, because she’s a real person, not just an imaginary one in your head.

So take the time now to disabuse yourself of the notion that you know what she’s like at all, and go into this date with a totally fresh mindset. Go into the date with the intention of finding out who she is – what makes her tick, what her likes and dislikes are, and whether you like that person or not.

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Above all, be relaxed and have fun. She’s going to have a good time if you’re having a good time, so make 100% sure to keep your mood light, playful, and happy. It feels good to hang out with people in a good mood, and it feels bad to hang out with people who are in a bad mood, so don’t f*ck that part up.

And don’t worry about awkward pauses either. She’s probably just as nervous as you are, so as long as you remember to keep yourself in a good mood and go into it with a healthy sense of curiosity, joy, and good humor, you’re going to be fine.

more: 40 First Date Questions To Have A Great Conversation

Or you’re going to sh*t yourself in front of the busboy. I don’t really care either way.

Anyone have advice for Geoff on his date? Any first date horror stories? Leave ’em below.

more: 101 Unique Questions To Ask On A First Date

And as always, if you’ve got any questions, send ’em here and I’ll answer them with a maximum amount of condescension and insults.

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