First Date Tips: Ask These Questions When The Conversation Slows

first date tips

If your first date is tanking or there are too many awkward silences, you have two choices: stuff food in your maw, chug your cocktail (or cocktails), get the check, and bail. Or give the first date one last push and try to pry some fun out of an otherwise dismal evening. That’s why having a few good first date questions in the chamber is a decent idea.

Clearly, “what do you do for work?” isn’t what we’re thinking about. It’s a boilerplate throw away that inevitably leads to a boilerplate answer. Then she’ll ask you and you can pretend your job is important or fun when it’s really neither. (If you disagree, you’re fooling yourself — or trying to, anyway.) Instead, try some of these …




#1. Which one of these statements is a lie?
Tell her three interesting things about you. Two of them should be true, one should be a lie. So, assuming you’re not into drag, you could say:

1. I went to high school with the Craigslist Killer.
2. I thoroughly enjoyed Pitch Perfect 2.
3. I wear ladies undies every other Thursday.

Those are examples, but the idea is to get her to let her guard down while dropping some info about you that can get a conversation rolling. Maybe she’s into Pitch Perfect 2. Or — even crazier — also wears women’s undies.


#2. What’s the worst movie you’ve seen in the past month?
Along with providing you with the types of movies she doesn’t like, her answer has an organic follow-up: “Is that what type of movies you’re into?” Movies are an easy thing to chat about, but don’t let the topic dwell for too long. Once you’ve explored this and given her the worst movie you’ve seen in the past month, use something she said to pivot to another topic. Read: listen to everything she says and find a snippet that’ll give you something to work with.


#3. If you had a choice to travel back in time to high school or college, would you do it?
Her answer can give you a glimpse as to whether she had a tough time getting along with people, whether she partied hard or was a bookworm, and whether she can think on her feet. There is no right or wrong answer, but if she can’t come up with anything, “Check please!” Hit the bricks. However, if she rolls with it and comes up with an answer, your return volley can’t make you seem like Peter Pan. So, don’t say, “Hells yeah I miss college. I got blasted every night and baked every day and hooked up with, like, five real live women.” How about this instead: “I miss college — Old School is one of my favorite movies, by the way — because it was nice to have to worry about studying and getting to meet people instead of paying bills and filling out TPS reports.”


#4. “If you found $10,000 and had an hour to spend it, what store would you go to first and what would you buy?”
It’s not exactly asking her to ponder the quandaries of world cultures, but it’s something that she really shouldn’t have to think too hard about. If she starts to stumble, rephrase the question so it’s easier to answer (so, eliminate the hour time limit).


#5. What’s your go-to karaoke song?
If she says she doesn’t do karaoke, it’s fine; pivot by telling her to choose a song she would sing if she were alone (depending on how comfortable you feel, you can mention singing in the shower). Spin this into asking about concerts — does she go to them, has she seen the person/band she just mentioned? It’s a more interesting way of asking her music preference, and allows her to share stories about her concert experiences (if she has any). If she doesn’t like concerts — and why would you be with this snoozer if that’s true? — it provides insight as to what you’ll be dealing with if she’s down to go out again.




Also Read: 5 Tips For Scoring A Second Date

second date tips