6 simple questions you're forgetting to ask on first dates that will tell you if you should go out again

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When you’re dating, the goal for most people is to eventually meet someone you like enough to see again and potentially date long-term. Which is why the conversations you have on a first date are so important — you get a chance to see if you two vibe together and whether or not your values are in line. There are some simple first date questions you should be asking to see if it’s going to work in the long term…or even just to make a bet about whether you’ll have a second date.

That said, you don’t want to interrogate a person. That’s not a cute look.

It’s always good to remember that first dates are totally awkward, and having a list of questions you want to run through can take all the fun out of getting to know someone. So you want to ~be cool~ if you plan on getting the best, realest answers from your date. Here are some good first date questions to ask that you might be forgetting.

1“What does your day normally look like?”


Instead of asking what someone does, which can be intimidating or boring depending on the person, ask someone what they’re schedule is normally like. An average weekday or Sunday is a good way to see if your schedule works with your own or if you have any shared hobbies. That way, you know way in advance whether a second time around is worth it.

2“How did your last date end up?”


This is great conversation starter, but will also give you some insight into their dating life. Are they playing the field? Trying to hookup? Looking for True Love? The most recent date doesn’t tell the whole story, but it will let you know why they’re dating in the first place and what they’re expecting.

3“Do you have a BFF?”


Asking about someone’s friends actually isn’t a first date topic all the time, and it totally should be. This is a good way to get someone to talk about their past, like how they met or know their besties. But it’s also a good way to see what their social life looks like and what kind of gaps they’re looking to fill with their dating life.

4“How long are you planning to be in town for?”


Seriously, this sounds stupid, but in the age of Tinder, it’s entirely possible you’re on a date with someone who’s simply in town for work or a short-term stay. Soon, they might be on the way to the next big thing. It’s so obvious that you might forget (and they might be a little sneaky and not want you to know off the bat), but you want to get an idea of someone’s permanence before your start setting the clock to wait for that follow-up text about going out again.

5“Do you like your roommates?”


If, obviously, they have roommates. This is important stuff! You want to get the lay of the land when it comes to their living situation. That way, later on, you’ll be better armed to go into the whole “your place or mine” conversation. Hey, knowing where you’re going to be able to have sex if turns out to be a great date is important!

6“What are you looking forward to these days?”


The immediate and near future is all you have right now with this person so far, so get in there and learn everything you can. Are they going on a big trip anytime soon? A friend’s wedding or their own birthday? All of these things can give you a better idea of who this person is and what makes them tick. It’ll also give you an idea of how a new person like yourself will fit into their world.

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