10 Questions To Ask On a First Date

I’ll admit it – I’m in my late twenties and I’ve been (mostly) single for the better half of a decade.

Being single in your twenties these days means lots, and lots, and lots of first dates. If you want! And trust me, there will be times when you want. There will be times when you go on all of these dates and you want to crawl into a hibernation pit and not date for months – because life is all about balance. But I digress.

There is a reason why we mostly find ourselves on first dates and not second dates – because it’s a waste of time to keep going out with someone when you know in the deepest part of your soul that it’s not going anywhere. What’s the point in getting ready and going out with someone you don’t see a future with? It’s much better to find this out right away than to waste even more time or makeup.

I’m sure some may read that and think it’s a quick judgment. Maybe it is. But I’m not saying you have to write off every person you don’t see yourself marrying (that shit takes time) – but I am saying, you know in your gut when you don’t even want to spend another coffee, lunch, dinner, movie, whatever with this person. Trust your instinct.

Here are 10 questions (both internal and external) you can ask on a first date so you don’t waste time on a second:

  1. Do you feel a connection? This is definitely an internal question – please do not ask this out loud. In the age of Tinder and Bumble it’s so easy to form an online connection with someone that just doesn’t translate to real life. Now, I know that this immediate spark isn’t everything blah blah blah, but I think that electric feeling is so important. If you don’t feel that connection when you meet someone IRL – take note. It could be the first sign that there shouldn’t be a second date.
  1. Who are your closest friends? Y’all, trust me on this one. Red flag one: they have no friends. You don’t want to date someone with no friends. Red flag two: they are friends with ALL girls (or boys – works both ways). Red flag three: they talk shit about their friends. Ask him to tell you about his friend group. Learning about someone’s close group of friends, or how they treat their friends, can say a lot about how they will treat you moving forward. It can also open up the conversation to a lot of new places. It may feel like a strange thing to ask – but you want to find out as soon as possible if you’re dating someone who cannot even snag one friend. Please note – dogs do not count as members of his clique (there’s a story here about a date I went on with a man who passionately described the tattoo he was going to get… of his dog wearing a baseball hat).
  1. What are you most passionate about outside of work? This is number one for me. There are definitely other ways to phrase this question but I hate asking people what their hobbies are. First of all, you shouldn’t be dating someone who has no passions. That’s boring. They’re boring. Sorry, it’s true. Second of all, this is the best way to get someone to open up. Once they start talking about the things that they love, that’s when you can truly see a person.
  1. Tell me about your family? My family is extremely important to me, so it’s important to me that my partner has similar values. Even if you aren’t very close to your family – it reveals a lot about a person to see how they talk about their family – close or not, sane or dysfunctional – and it’s best to get this out of the way initially. My last boyfriend had a very toxic relationship with half of his family, and I didn’t find out until it was too late. Again, this isn’t about dumping anyone who has drama going on within their family (because who doesn’t) – it’s about how they handle it.
  1. Where was the last place you traveled? Not everyone has the travel bug, or even has the means to travel, but I do think most people like some adventure in their life. If you’re dating a dud who never wants to leave the city you are in ever, it’s good to find that out now.
  1. What was the last book you read? Other versions of this include: what’s the last movie you watched, last time you went to the gym, etc. Basically – you want to make sure you will have some shared hobbies. I was once dumped because the boy said he “never saw himself dating a girl who reads.” Really? What this taught me was that this guy was a total dick, but also that I need to date someone who appreciates my passions, even if they don’t share them. By starting a dialogue about things you’re into, even if he doesn’t share them, you can see how he responds. If he laughs, makes jokes, or puts you down when you share something you love – trust me – get out.
  2. Are you single? This may seem like a joke but in all seriousness, I have been on two dates with dudes that had girlfriends. Like actual live girlfriends. It is important to make sure that the person you are spending your time with isn’t using you as a backup / side chick / undercover lover. People can be shady, do your research.
  1. What is your biggest goal in life right now? Whatever age you are, from 16 to 67, people have goals. This could be a short-term goal, something like trying to work out 5 times a week for a month. It could be saving for a house. Going back to school. Could even be as simple as keeping a clean apartment. Everyone should have goals. This will open up an interesting dialogue with your date, as well as let you know if this person is completely stagnant. Like I said – this does not have to be something huge. But you want to be with someone who is striving to improve or move forward, in one way or another. If they don’t have any goals for their future, they probably aren’t in a place to date anyways. Harsh but very, very true.
  1. Is he asking you questions? This is also an internal question to ask yourself. I went on a date a few months ago with someone who legit did not ask me a single question all night. Though I could tell you what his weekly meal plan and workout schedule looks like. There was absolutely not a second date with this one. Pay attention to this – if he’s interested, he’ll ask about your life.
  1. What do you like about him? Also internal. Also important. I went on a date recently that was fine – we had drinks, no lulls in conversation, I laughed a few times. After the date I told my friend I would go on a second date if the opportunity presented itself and my friend asked,  “What did you like the most about him?” I realized that I didn’t have an answer. There was nothing I liked very much about him. Needless to say, there was no second date. This struck me as enlightening – if you don’t notice something in particular that you like about HIM as a person, you are probably just dating for dating’s sake. Or free food.

This is certainly not the foolproof list of ways to figure out if there should be a second date – but they’re a good starting place!

The most important thing is to pay attention to your gut. The right dude is out there, and with the right dude, you will not question even for a second whether there should be a second date.

This Landlord’s Letter To 5 Girls Who Are Definitely Not Getting Their Deposit Back Is Brutal
This Landlord’s Letter To 5 Girls Who Are Definitely Not Getting Their Deposit Back Is Brutal
  • 10614935101348454