First dates are a little bit like going on a college tour. You get to see the glossy, brochure version of a person's life without committing to ever setting foot on that campus again. Your first date conversation topics should hit all of the major aspects that are most important to you in a relationship, while also staying open to new possibilities that might intrigue you. Think of it this way: If you wanted to become a painter one day, you wouldn't sign up for a school that doesn't have a fine arts program. But you wouldn't decide against a school just because you have to take algebra as a prerequisite.
Like college, new relationships are a way in which people embark upon new chapters in your life. If you are dating with the goal of finding a possible long-term partner, then you know that nothing will ever go as you initially planned. Treat the conversations you have on your first date as a low-key way to get the lay of the land. You don't need to make any snap judgments, but you should definitely see if you and your date are on the same page. If you find that your histories are at odds with one another, then you don't want to waste your time on a second date. Why would you pay the fee to apply to a program that you wouldn't even enjoy?
Here's what you should talk about on a first date to determine whether you want to have a second one:
These days, politics might be the last thing that you want to discuss when you are trying to have fun on a date, but it's important to say something political nevertheless. Even if you and your date vote along the same party lines, you might be insulted, offended, or even threatened by their political beliefs. You might even have similar value systems but still find your date to be abhorrent. For example, one time, I went on a date with somebody who mansplained gentrification to me. I know what gentrification is, and I wouldn't have gone on a second date if he had paid me.
You don't have to get into an intense theoretical discussion, rehash the election, or talk about whether or not you registered to vote in the primaries. Drop some breadcrumbs about your political belief systems and see whether or not your date picks up on them — and whether they jive with what you are saying — to determine whether a second date would compromise your values system.
2. Family Background
Whether someone came from a happy home or not should not determine if they are a compatible partner or not. However, their upbringing will influence the way in which they approach relationships. Depending on whether they were raised by a single mother, parents who stayed in an unhappy marriage, or born into a religious commune, the way they were raised will shape their outlook on love and partnerships. And don't forget about birth order. Dating an only child is much different from dating someone who was raised with five other siblings. Ask about their family background and childhood to get a glimpse of where they came from and what it taught them about love.
3. Best Friends
Personally, I would never trust someone who didn't have a best friend they valued as much or even more than romantic relationships. On a first date, talk about your best friend and see how closely they pay attention to what you are saying. Do they seem to care to learn about someone who is close to you? Or do their eyes glaze over in boredom? Do they also have a best friend they want to gush over? Or do they claim that they haven't been platonically close to anyone since Kindergarten? Their social life might not be a deal breaker, but it will give you a glimpse into understanding how your date forms lasting intimate relationships, and whether it sounds like something you want.
4. Living Arrangements
Do they live in a Manhattan loft or are they in an open marriage, sharing an apartment with their wife? How a person lives at home can give you insight into their financial life. Again, money should not be a deal breaker, but if someone's living situation reveals they have significantly more financial freedom than you, it's fair to question their generosity if they make you split the bill. Understanding a person's living arrangements also gives you a feel for what to expect from a relationship.
If you are seeing someone who is in an open marriage, for example, knowing the terms of their at-home situation will provide you with some measure of transparency. Even if you're in a more traditional dating situation with someone who is in the same tax bracket as you are, hearing about who they live with will give you some insight into their social life. Have they been through five different roommates in the last five years? That might tell you they have some issues with interpersonal conflict or forming stable relationships. Again, it's not necessarily a deal breaker for a second date, but it would provide some valuable information as you decide to move forward.
If you want to know what's really in a person's heart, ask them about their pets. Even if they don't have their own animal right now, lots of people form bonds with their parents' dog or roommate's cat, or at the very least, they can tell you a story about the parakeet they had during their childhood. Someone who doesn't demonstrate any empathy toward animals always raises a red flag for me. They don't have to be a vegan in order to demonstrate having compassion. Paying attention to how someone takes care of the smallest creatures in their life will give you a great deal of information about their emotional depths and will let you know whether or not they're too shallow for you to make it work before you take the plunge.
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