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I think some of the suggestions regarding past relationships are a bit heavy for a first date.
I’d hear about their interests, passions, dreams, and life goals and values first. Keep the conversation positive and dive deeper deeper during date 2 or 3.
This can be an awkward topic but I think asking about someone's first love can tell you a lot about them. Some people are still holding on to resentment, some people are not over their first love, or they may hold a lot of trauma that came from that relationship. It's good to know that upfront so you don't get surprised by being called the wrong name in bed 3 months later (true story). Best of luck on the date
I feel like first love might be way behind you at 30 plus unless you lived a very shielded life… maybe re last serious relationship, could be more accurate?
Ask about money. Kind of a tough topic for a first date but I think asking about their financial goals can help you determine from the start if you're compatible or at least on the same wavelength.
I ask them about past relationships. We’re they married, why did it fail, what was their longest relationship, how long have they been single, etc. I like to hear how they talk about the failed relationships and dating in general. Do the blame all last relationships on the ex sucking, or do they take a fair share of the blame. Do they sound resentful or spiteful or do they sound like they’ve moved in in a healthy way in their mind? Do they think all men suck and make sweeping negative generalizations, etc. I want to know that they’re a true partner and are in a good mental space to enter a new relationship.
Tbh if the date was largely this, I’d feel under undue interrogation, judged no matter how you react, eventually bored as fuck, and not seeing you again (I’ve never fled mid-date but maybe I would!).
Fair topics but we also need to laugh and feel out sense of humor, bring forward what we enjoy in life, etc.
I ask them to tell me about her their best friends. How did they meet? What does she like about them? What do they like to do together?
If she struggles to name a friend or activity, or if the friends has kinda only been there to ease emotional labor, then that says a lot about what she’s expecting from a relationship.
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I like to ask what they do for fun, how they spend their free time, or what hobbies they have.
While all recommendations above are reasonable, if you simply ask these things in a straightforward manner, it can make the conversation a bit dull. You want to elicit a sincere response and also make it fun, so you should care about the format too. Try to gamify the process by laying out different scenarios and asking what she prefers. Try to make bets on whether you can guess certain facts from her past by analyzing what you already know - this will make it fun but also highlight the stereotypes you may have about people and where you tend to misinterpret things. Ask her what she thinks other people misunderstand about her - this will make you connect on a deeper level. Etc., etc. As for the content - another important thing is to understand her decision-making process - how independent she is in her judgement vs relying on what her family/friends/support group/society says, so offer a bit more extreme scenarios to react to and see what her thought process is. This is kind of intense for the first date, but at least not intrusive - not everyone is willing to discuss their past relationships, and not everyone will say the truth about them.
Well well congratulations Sr!!
I think it depends whats important for you.
I think I read in a few places you should be dating for fun instead of commitment in the beginning.
This means to me that instead of trying to vet them instantaneously see if you get along as two individuals. After all, that will be the make or break years to come.
Thereafter you should see if you align on the things that matter to you.
This might be money, but it might be if they take your last name. These can be very different to each individual.
Whilst I think ‘marrying your best friend’ is extremely overrated, I find it to resonate with me on the level that you do wish to be a with someone that will be you friend (as it feels right to you) through thick and thin.
Ask them how they’d describe their upbringing. Was it comfortable, a struggle, fun, stressful? Check for their awareness of how their upbringing impacts the way they show up in the world.
That's great! How did it go? As much as possible, I avoid asking questions such as about past relationships or exes.