So I (22f) am going on a first date tonight and I’m trying to date for intention. I don’t want wedding bells right away but I would like to meet a nice guy to call my boyfriend. What questions should I ask on the first date without sounding too intense?
Comments
Determine if he comes from a good family. “Tell me about your parents, siblings” etc.
In my opinion, on one side you should ask important questions of course, on the other side it can become quickly an interview and kill the vibe completely. Also he could answer everything perfectly but there’s no vibe between you and him.
I feel the best is not to ask per se, but let him give you the answer indirectly, otherwise you risk that he will try to answer what you want to hear.
On the first date I like to mainly keep the conversation around hobbies, passions, what is he looking forward in the immediate future. Keep it lighthearted, don’t go into deep conversations, you can touch a bit on topics like how is his relationship with his family, if he has siblings and so, what kind of life he would like to be in 10 years too by example.
Also be mindful of what you share with him, don’t overshare, don’t talk about insecurities, past exes, if there’s any topic he brings out and you don’t want to share a simple “I don’t feel comfortable talking about this for now, I prefer to know you better first” or similar is enough. I used to over share a lot in the past and regretted it, now I am careful of what I share, in the end that man is a stranger still.
I pay a lot of attention to actions although, is he kind with the people around him (specially waitress and so), is he a gentleman, opens the doors, pays the bill, has good etiquette, is he listening to what I say and seem curious about my answers or he only wants to speak about himself, do I feel comfortable in his presence, I enjoy his company, and so. Those are for me, but you can have your own set of attributes that you wish on your future partner, pay attention if he does behave aligned to those.
I would say if after the first date it was pleasant, then slowly on the following dates you can ask more personal questions. And take your time knowing him and letting him prove you he is worth of your time, he has to put effort.
When I (53m) was 35-ish, I went on a first date with a woman. During that date, she said to me, “I want to be married and have babies. I’m not rushing you or anything, but in six months, if this isn’t really progressing, please don’t string me along. Will you just tell me?” We did, in fact, date for about six months. Something came up that I was uncomfortable with and I reevaluated the relationship. I told her that while things were going fine, I didn’t see this progressing and that we should stop and move on.
So I think you could/should modify that a bit for your circumstances, but why not just be direct about it?
(I dated my wife next and she next dated the man she married and had babies with. It worked out for both of us.)
Ask observational questions too.
Example, my man was wearing a hat and sunglasses. I said, “if you had to choose 1 accessory because you couldn’t have both, which one would you choose? Why?”
He was also writing with one hand but eating with a different hand. I asked about which is dominant / if he is ambidextrous.
Maybe it’s because I’m in my 30s, but if it’s not obvious where they lie politically, bring up politics. Don’t waste my time and I won’t waste yours. The last thing you want is someone who starts blabbing about Andrew Tate once you’re invested.
If you have pop culture stuff in common, there are usually questions about that which can be fun and also interesting to think about. Like the Harry Potter questions: Which house would you be sorted into? What would you see in the Mirror of Erised? What would a boggart look like for you? What would your patronus be? (Harry Potter has gotten kind of complicated since JKR started saying such horrible hateful stuff, which is terrible because it was such a big part of growing up, but I can see why you might want to avoid it.)
A guy I met online asked me which member of the Gaang I would want to have lunch with, which I thought was a good question. (That’s a reference to “Avatar: The Last Airbender” which I mentioned on my profile which meant that he read my profile and also he knew something about the show.)
Maybe ask him to name three fictional characters he would want to be like and why, and then you can do the same. (I would say Cordelia Naismith from the Vorkosiverse, Winry Rockbell from FMAB, and Kaywinnet Lee Frye from Firefly.)
don’t treat it like an interview. just share the things about your self/life/values that are important to you and open the conversation to hear his opinions as well. asking super specific questions can make it seem like there’s a “right” answer and can just mean he’ll say what you want to hear.
ask questions to yourself and find out the answer through his ACTIONS, i.e.:
a) is he listening to you and interested in what you have to say?
b) is he a forward and empathetic communicator? is he sharing valuable things about himself that help you understand him and receptive to you doing the same?
c) does he talk about others positively or non-judgementally? or is he bringing up exes and strangers in a negative light totally uncalled for?
d) how does he talk about women?
etc.
keep things open ended so he can explain what’s important to him more organically. look for similarities and differences. look for signs of a good communicator and partner. it’s really just a normal conversation lol
the truth is you can’t find out everything you need on a first date. people take time to open up and that’s normal. rn just focus on how you feel on this date and whether or not he makes you feel safe and comfortable (which can take time to be sure of). if something makes you uncomfortable, throws you off, gives you pause, etc. it’s always okay to slow down or stop altogether. dating with intention means moving on when things aren’t gonna work out
Ask about his mom, how he treats her is how he will treat you. The amount of things she does for him without him asking is also what he will expect.
Find out about his values, discuss subjects that are important to you and leave him room to reveal how he feels about them. Rather than stating your position on the subject where he might just agree to be safe, state contradicting outlooks and ask which resonate with him and why.
His underlying beliefs will likely reveal his personality and expected behaviours.
Are you meeting these guys through apps, in person, or through friends/family? Another way?
I’m 36M, I can tell you my experience. My fiancee and I had figured friends only, she later told me she’d been open to FWB. I was poly and partnered at the time, and disclosed this before our first in person meeting. Etc.
(Fiancee interjection – she says have the guy answer questions first, and don’t tell him everything! Especially not your traumas, insecurities, etc.)
She asked me questions about my values and beliefs first as an initial filter, some about my current/future plans and my dreams, etc. This happened over chat and again in person, I assume she was looking for consistency. She’s had an ex mask for years before becoming abusive, so she’s cautious about that and took about 6 months to fully let down her guard. I also discussed my recent history in therapy and the progress made, which to her and many of my prior partners has been a huge green flag. But also, be warned, some unsafe people do weaponize therapeutic language and concepts.
Part of what made her feel safe, according to her, was that I admitted to being problematic in the past. It made her nervous too. Trust your gut – in this case, she gave me a bit of time to show that I’d grown past that part of my life.
In her words, I hit her like a Xanax and quieted the chaos in her brain basically from the get go. So an hour into the date, she told me about some of her recent work history, and we talked a lot. We moved pretty fast because we’re older – but that breaks a lot of our usual rules.