First dates can be tricky. No kidding, right? On the one hand, you want to make a good first impression, but at the same time, you also want to come away from the experience knowing if you even want to see them again. It’s a real balancing act because you want to play it cool and not come on too strong. But what is the point of a first date if not to weed out incompatible matches? To that end, it’s good to have a few questions about their goals to ask on the first date. Ones that are subtle enough to pass as regular conversation — or to naturally open up the conversation for follow-up questions — but will give you some insight into what your date envisions for their future. That way, you aren’t weirding anyone out, but you’ll still have the opportunity to know if you want a second date to be one of your future goals.
Not sure what to ask? No worries, I’ve got you covered. Next time you are on a first date that seems like it has the potential to go somewhere, here are some questions to ask that will help you gain some insight into their goals and plans for the future.
1What do you like about your job?
A first date is, in a weird sense, an interview. It’s almost like they’re "interviewing" to be a potential love interest or hookup, so you want to make sure they have the ~qualifications~ you’re looking for— whatever they may be. But despite having things in common with a job interview, a first date should never actually feel like one. So, if you want to find out what this person’s career goals are, rather than outright asking that and killing the vibe, ask them how they feel about their current gig. Depending on how they answer, you can learn plenty about what career path they’re on and their plans for their future.
2What is something you’ve done where you’re like, “Yeah I did that!”?
Along with learning what your date wants to do with their life, you might also want to know the odds of them actually pursuing and following through with those ambitions. In a job interview, an employer would most likely ask something like: “What is an accomplishment that you are most proud of?” Great for an interview, but not exactly sexy on a date. So, while the question is in essence the same, the phrasing here is warmer, more conversational, and more likely to get an honest answer.
3Where is your favorite place you’ve traveled?
Someone who has no interest in travel is kind of a deal-breaker for me. Not only because I really do love to travel and want to do a lot more of it in my lifetime, but because if someone doesn’t want to travel, it feels to me like a lack of curiosity, which just isn’t something I’m personally attracted to. I definitely want to know if traveling is one of their future goals. Rather than just asking straight up if they like to travel, I prefer this more open-ended question. Even if they haven’t done any traveling yet (hey, it isn’t cheap!), you can gauge their eagerness to travel in future.
4If you could, what famous person’s life would you steal?
Want to know what this person’s ideal lifestyle would be? Ask who’s life they most want theirs to be like. This might help you gauge what they value most. For instance, is the person they admire someone with a big family? Someone who is self-made? Highly educated? Problematic? While this may not provide you with specifics of their life goals, you can pick up a general idea of their plans, or at the very least, hopes for the future.
5Do you come from a big family, and are you close?
A first date is probably not the best time to be talking about whether or not you want kids. However, if that’s something really important to you, you can still get a vibe on how your date feels about having a family in the future by asking about their family in the present. It’s not as definitive an answer as simply asking if they want kids, but it’s a lot more likely that you’ll learn about what they want while still keeping it casual.
While these questions probably won’t solve all your first-date anxieties, they can at least make getting to know your date in a real and important way a little bit easier — and hey, every little bit counts.
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