My friends know I ask inappropriate questions. I ask these questions in the most straightforward way possible and usually without ulterior motive. I am genuinely curious what people’s salaries are and how much is their rent and how old are their parents. I freely offer up my own answers to these very questions: I make $28,000/year, pay $550 in rent, and my mom would disinherit me if I shared her age.
Maybe it’s because I’m not trying to hoodwink anyone, but people generally tell me the truth. And I’m talking strangers disclose personal failures after one inquiry. I once helped my friend pick up a couch from a Craigslist seller. By the end of the interaction, I knew the seller’s hometown, graduation year, and why he and his girlfriend broke up (it was originally her couch).
However, asking these types of questions can sometimes get you into trouble or, at a minimum, leave the wrong impression.
I recently went on a first date with a woman I was really into. We matched on Bumble, and from the first hour, became incessant texters. That is not my MO at all. I typically am the person who messages, “I’m so terrible at checking this app,” after three days’ radio silence, which instead means, “I have no interest in asking you out; I’m just bored so I’m going to kick this convo down the sidewalk for a bit.” Instead we meandered varied topics without dead ends or stale lapses.
Our first date lasted five hours. We rock climbed and ended at a rooftop bar. I asked her if she wanted to get dinner, but disclosed I wasn’t trying to kidnap her. We decided to stop while it was still a good thing and made plans for the next week.
We had two more dates that I would label also above average. I didn’t believe online dating could work so well. Then she sent me a breakup text.
“Hey, Cazey, I know this may seem too soon, but I don’t think this is going to progress romantically. You are great, brilliant, funny, handsome, a deity among men, but I don’t see this being long term.”
Okay, she didn’t call me a deity. I would’ve been spooked. But she did give me a list of gratuitous adjectives that I would be sure to add to my dating profile: “Previous dates have called me…”
I was confused. If I was all these things, then what went wrong?
I began to relive our interactions and discovered a series of faux pas I had made. Why did she think I wanted long term? I’m moving in less than six months. I’m a commitmentphobe. Where did she gather these signals?
Below are my tips for what not to discuss on a first date, especially if you aren’t trying to get married next week (sorry, Mom). These tips come with a lot of hindsight bias and also some justification for why I would even bring up such things up (because it’s me?).
Don’t ask about kids.
This is peak me. I ask everyone if they want kids. Apparently first dates are not the setting.
While on the rooftop, I asked my date if she wanted kids. And how many. And does she have any names already picked out?
Honestly, this is more about assessing one’s personality versus trying to sire some kids. If you want five kids, I doubt we’re going to really connect.
Don’t ask how you fit into their 10-year plan.
Now I am not so insufferable that I’ve ever asked someone what their “10-year plan” is, but I am definitely someone who asks, “What do you do? What’s that look like long-term? Oh, so you want to stay in Richmond? What’s your eventual median salary?”
Just kidding…maybe not really.
I’m curious what drives a person, what are they striving for, what are their dreams.
I think I need to start prefacing such inquiries with, “I’m not asking to be part of your 10-year plan for at least another 15 years.”
Don’t show up with flowers.
On our second date, I picked up my date and brought her a bouquet of flowers. I immediately told her I got the flowers for free from a fundraiser I helped plan, aka “don’t read into this.” But that doesn’t mean I didn’t pick up my date with flowers like some late ‘80s romantic comedy.
I even said, “I have more flowers at my apartment if you want to trade them out for a different bouquet.”
Don’t pay for everything.
When my date and I went rock climbing, she had a Groupon so we paid nothing. This led me to pay for rooftop beverages as a thank you. This isn’t a lot to cover, and it was a first date…but then I also insisted on paying for everything on the second date…and dinner on our third.
I really can’t explain this behavior because I am a cheapskate. But all I can say is, go halfsies at least sometimes to emphasize you’re not here for a long time, just a good time.
Don’t tell them you’re moving to a new city and ask if they’ll follow.
Okay, so the latter did not happen, but I did tell my date on the third date that I was moving in March. This is a previously undisclosed fact for both readers and my date.
The fact that I’m moving is what it is. It can complicate dating if they’re thinking for the long-term, but it’s also why I’m not looking for something serious..
However, I didn’t want to be that blunt, and I also overcompensate when I share harsh realities.
I think I delivered the news like this: “I should probably mention I’m moving in five months. I’m not going that far away, so like, it doesn’t need to be a big deal. And isn’t your job mobile? Or you were looking to change jobs? You could always follow me if things work out.”
Okay, again, not my exact delivery, but I do think I tried to soften the blow by working her into a narrative I’m not sure either of us wanted to be part of.
I also don’t recommend telling them while you’re making out on their couch. “Hey, stop for a second…”
No, I need to stop.
Don’t make travel plans.
I am one of those people who is immediately like, “We should go!” when people talk about a destination. This is even more true when drunk.
On our second date, I found out my date hadn’t been to New Orleans.
Me: “We have to go!”
I also discovered she loved Montreal.
Me: “It’s amazing! We have to go back.”
Did I mean these things I said? Probably not. Did they sound very long term? Mm, yeah.
Now let’s cut back to when I received the breakup text. Because I hadn’t been thinking long term, I questioned the heaviness of the text. Did this really need to be said? Had we invested that much in each other? Because I sure hadn’t. I replied something to the effect of, “I appreciate your frankness and think you’re cool too,” (yes, I used the word cool), “I’m not seeking anything in particular, so this isn’t a big deal.”
Which is when she disclosed all the red flags I had thrown out that led her astray into thinking I wanted something serious. In the end, we went on a few more dates before a real breakup was reached. The final breakup felt more justified than the first in that it didn’t involve how many kids we did or didn’t want.