The shortest date I ever went on was fifteen minutes. Drink orders weren’t even taken and coats were barely unzipped by the time we both looked each other in eye and the braver one of us, probably not me, said maybe we should call it a night.
It wasn’t that we weren’t attracted to one another. He looked exactly like he did in his photos on the dating app, and I like to think I look similar enough to mine that a guy knows what he’s getting himself into when he meets me in person.
The date ended because somehow, in the first couple of minutes, we both skipped the mutually agreeable topics like the weather and how annoying our commutes were today and jumped right into politics. Before menus were placed on the table and the waitress could tell us about tonight’s specials, we were in a heated debate about whether or not Obamacare was a good thing for our country.
One of us said yes, the other said no—and then we both pretended like we were up at a podium during a presidential debate, where we could tear into each other with harsh comments and rude back-and-forth banter.
I was rather new at dating during this time. I had only been on one other date that year, and it was already September. I knew that there was a short list of things that shouldn’t be brought to the table on a first outing, religion or politics chief among them, but sometimes you find yourself sitting in front of someone who can’t keep their mouth shut about one of those things either.
From that moment on, I’ve worked harder to make my first dates last longer than it takes to watch a TED talk. Which is why I’ve found myself suffocated with nerves to bring up certain topics on a first date that I think may lead to the guy asking for the check prematurely or just going off on a rant that I’m not in the mood to hear.
This is my list of 4 things I’m scared to tell guys about myself on a first date—and what’s happened in the past when I’ve tried to bring them up.
1. I Work For Myself
I’ve never been on a date where the question “Tell me more about what you do for a living” didn’t come up. Though I’d rather talk about that than have someone ask me what my imaginary five-year plan is (what is this, a job interview?), it’s usually the kind of topic that puts me on the defense, since I’m my own boss and I work from home. When I explain to guys that I’m a freelance writer and an entrepreneur, they usually ask me when I plan to get a “real job” or if I actually have a business that’s profitable. That’s the moment when I find myself on the edge of my chair mouthing off the elevator pitch for my start-up and then my monologue about why I’m an independent woman who is proud to hustle to make money doing what I love.
2. I’m a Vegetarian
I used to casually mention this while pining over the menu on a date with a guy I’m meeting for the first time. But I found that 80% of the time, after I said this, the guy would launch into a full-out campaign as to why and how they will get me to eat meat again if we start dating. A fun fact is that I haven’t had meat in 22 years—which is why, when a guy would say that to me, I’d roll my eyes, pick up my drink, and toast to the fact that they clearly have no idea just how stubborn the woman they’re feasting with is.
3. I Don’t Plan on Staying in My Current City Forever
I’m from Florida, have lived in California, and only moved to New York City a couple of years ago. I have dreams of being a nomad for a little bit before settling down. Telling someone you’re potentially going to fall in love with that you’re not sure where you’re going to be living in 6-months or a year can be quite the red flag to raise on a first date. But because I’m no good at lying, when the question about whether I’ll stay in New York for a while comes up, I usually just say that I love it here—for now—hoping that they get the hint I could be ready to pack up and go eventually.
4. I’m Not Still Fully Over My Ex
There’s really never a good time on a first date, or a second date, to tell the person you’re sitting across from that you’re not 100 percent over your ex. That’s the whole reason I downloaded five dating apps and am putting myself out there. I’m trying to get over that person, but am I really ready to stop checking out their Instagram feed or delete them from Snapchat? Um, no. I may need another few months for that.
