You’re going on a date tomorrow. Maybe it’s a first date, or maybe it’s a seventh (good for you!), but either way, you’re likely to have to make conversation with the person sitting across from you (or bowling in front of you, or hang-gliding below you — I don’t know your life!). One easy trick for making conversation is to ask questions (this seems obvious to me, but I have met men, so, you know), so whether you know someone well or you’ve just met, I made a handy list of questions you should ask on each date.
Questions on a date are a great way to get to know someone because you get to bring up topics that might not come up seamlessly in conversation. For example, I once asked a guy if he had any pets, and it turned out he had a chinchilla, which is something I never would have learned had I not asked (he assured me they were legal, but he also seemed like he didn’t want to talk about it, so who knows). Just remember — if you’ve asked someone one of these questions before the specified date number, that’s totally fine! These are just ideas, but only you know how the cadence of the date is going and what questions are good to ask.
Read on to find nine questions to ask on each of your first nine dates to really get to know someone!
First Date: Do You Have Siblings?
This is a fairly innocuous question to get a conversation started. You might not want to advance to too many dates and then realize you still don’t know if they had siblings, so ask early, and use it as an opportunity to learn more about their childhood!
Second Date: Do You Like Your Profession?
Asking if they like their profession gives you a sense of their ambitions and what they see for the future. If they don’t love their job, they’ll be grateful you gave them the chance to commiserate, and if they love it, they’ll be happy to share! They might not have a job right now (or they might have multiple), but asking about their profession leaves open the possibility to discuss more than just a job (for example, they might consider their artistic passion their profession).
Third Date: What Are Dealbreakers For You?
Get this out of the way early (but not too early, in case it they don’t want to talk about relationship-related topics yet). If something about you is a dealbreaker, you might want to know that around date three. Besides, sharing dealbreakers can be a great thing to laugh over, since you’ll be able to open up about the time a man wanted to grow tomatoes in your scented candle (or was that just me?).
Fourth Date: What Are You Looking For In A Relationship?
You don’t need to ask this in a way that pressures them into telling you if they want a relationship with you (and who knows if you want a relationship with them!). But if you’re looking for something casual and they’re looking for something serious, it can be nice to find out sooner rather than later.
Fifth Date: What Issues Are Most Important To You?
By your fifth date, you can definitely start getting deep (although getting deep earlier is fine, too!). Ask what they care about most, whether it’s politics, social justice, religion, etc. And share yours as well — these are called passions for a reason, so people typically enjoy talking about them.
Sixth Date: If You Had A Million Dollars, What Would You Do?
Ask what they’d do if they didn’t have financial constraints and you’ll get a good idea of what their ideal life looks like! This is a great question to ask on a later date to find out about any dreams they might not share up front.
Seventh Date: What Happened In Your Past Relationships?
This is a great question to ask on a later date when you’re getting to know them on a deeper level. A relationship that ended isn’t a necessarily a failure, and it doesn’t reflect badly on someone. Still, asking them about past relationships is an easy way to open up about your history as well, and to figure out if there seem to be common threads.
Eighth Date: What’s Something You Usually Don’t Tell People?
This can be a regret or a secret dream or just a silly story, but it can be a good way to show intimacy with someone. Admitting something you usually keep secret brings you closer together. Don’t force it, though — if they seem uncomfortable sharing, switch gears.
Ninth Date: Can You Pass The Guac?
By date nine, you’ve probably run out of things to talk about. Just kidding! But you’ve gotten to know someone, and your questions are probably more specific to what you already know about them. Even if they aren’t, that’s totally normal and doesn’t mean you don’t have chemistry. But you still want that guac, you know?
Asking questions on dates can be tricky — you want to seem interested and conversational. Fortunately, as you get to know someone, you get the chance to ask more questions, which is part of the fun of getting to know a new potential partner! So enjoy your first nine dates, and always, always, always enjoy the guac — I know I will.
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