Avoid These Classic First Date Mistakes

Avoid These Classic First Date Mistakes

We’re all looking for different things on first dates, especially those arranged via dating apps rather than through a wise village matchmaker. Maybe you’re just trying to hook up. Maybe you want true love. Maybe you want something in between — like a sex friend, who will feed your cats while you’re on holiday. Whatever it is, I think we can agree that making a good first impression is important.

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After going on close to a hundred first dates, I have some perspective on what went wrong and what went right.

Now, before you go wild on me in the comments, I will say some of this advice includes generalisations about gender. I’m a cis woman, I identify as bisexual on dating sites and when it seems appropriate to do so out loud. But I date people all along the gender spectrum.

Some of the observations shared here about how men and women act on dates might not match exactly with your experiences, but they’re taken from a varied sample of a metropolitan population. With those caveats, here are some mistakes my dates made, and some I definitely made. Learn from our missteps:

Overly High Expectations

You can tell when someone shows up with really high hopes. And expecting to meet someone cool and nice is a great perspective to have. There’s no reason to meet with someone if you’re going to give off an attitude, or seem half-asleep from dating apathy. The other side of that is having such high expectations you freak someone out.

Don’t joke about your future together before you’ve finished your drink, and don’t make huge statements about what kind of person your date is before you’ve even found out if they have siblings. “You seem like you’d be a great at raising children”, or anything of that nature is a NO. One time a guy I’d never met looked me up on Facebook and commented on all my public posts. Get to the date, don’t get blocked.

Trying to Get Too Serious Too Quickly

On that note, let’s say you like each other and have decided to meet again. Awesome!! Now be normal. I’m not talking some three day rule BS about texting or any other trick to keep the other person on their toes. Just make a plan in a reasonable amount of time and follow through.

Excessive texting, immediately friending them on Facebook, or unsolicited pictures of genitalia will probably end in the other person either feigning an extended illness or blocking you. Though I never texted anyone naughty pics (without a request), I did blow my chance with someone by texting them too much. If someone says they’re away for the weekend, don’t text them on Thursday afternoon to see if they’re free Monday.

At least, I’m pretty sure that’s what weirded him out. Should I text and double check??

Bringing Your Baggage

Dating app bios feel like a secret language. It must mean something to the right person when they read their match is “fluent in sarcasm.” That doesn’t do it for me, and that’s fine. However, there is one style of “About Me” that I think should be abolished for everybody: showing your wounds. If you are an adult human looking for love, you’ve probably been burned before. Bios that say stuff like “no liars or gold diggers” are alarming and bringing old resentments on dates is going to ruin them before they even get started.

These are things to work on in therapy, but the first step is self-awareness. If your profile and first date conversation largely revolve around how horrible love and dating are, you’re waving a big red flag, and potential love interests will act accordingly.

Talking Politics

We’re living in a time where everything feels political, and I for sure don’t want to go home with someone who turns out to be wearing MAGA underwear. But before you get too deep into whether or not Bernie would have won, ask yourself, can I carry on a respectful conversation with family members about this issue? If the answer is no, what are the odds that you will be able to have positive political discourse with a virtual stranger?

Maybe you can, and that would be hot. Maybe you want to weed out anyone you will never politically align with. And maybe you could save that for date number two, when you have a little more context for the human being sitting across from you. If you do want to just go for it right away, at least let them finish their drink first. I really wish I’d had more than a sip of wine when one of my dates started with, “You know, I think we’re better off with Trump in office.”

Not Asking Questions

OK, here we go! This will get push back, probably from mostly cis men. Y’all don’t ask questions. At least, not when you’re on dates with women. I have found that even if I am not super attracted to a woman, we will generally have a pleasant evening, full of polite back-and-forth, active listening, and supportive comments. It is extremely rare to go on a date with a man and for us to part ways knowing the same amount about each other.

I have two theories about this. One is that when men are nervous, they think the best way to impress a woman is by talking up their accomplishments. Once a guy actually asked me to guess how expensive his jeans were. The answer was $500 and frankly, I thought he should be ashamed! My other theory is that men are socialised to think what women say isn’t that important, especially women they’re trying to have sex with.

Agree, disagree, get insanely angry in the comments. Just please know that you’ll always get a lot further on a date by occasionally thinking, “I’ve been yammering about my cross country road trip for a while, maybe I should ask this person where they grew up.” Then listen to the answer, and ask a follow up question. You’ll be more likely to win over the person sitting across from you, and also, you might actually find out something interesting about their life.

Not Offering Up Information of Your Own

After a lot of dates where I felt some resentment about the above phenomenon, I made more of an effort to share info about myself, instead of asking questions. It can be hard to extend yourself that way if you’re not used to it, and I caught myself holding back without any good reason.

Some people would divert things back to themselves immediately no matter what, but some seemed relieved to not have to think of something to say or ask, and it led to a realer conversation. If things have stalled, don’t forget you can take some pressure off your date by talking about something you actually care about.

Being Too Aggressive

Being on almost every dating app, some with reputations more for romance, some more for sex, I get propositioned all sorts of ways. Though I was going on two dates a week, in the first three months of that experiment I only slept with two people. You know what they both had in common? They didn’t pressure me at all. In fact, I explained to the second guy that it was his relaxed attitude that made me feel comfortable with him and he straight up told me that was his usual (extremely successful) action plan.

I suppose treating getting laid as a strategic enterprise is a bit clinical, but it’s also true that most safe, sane people don’t want to hook up with someone who doesn’t seem like they can take no for an answer. I once walked out on a guy who started touching me very intimately almost as soon as I sat down. Seeming confident, yet ok with nothing happening, is sexy — but only if you really mean it.

Not Saying What You Want

While it’s important to avoid excess aggression, being direct about what you’re looking for is also important. You don’t have to tell someone you’d like to get serious before they have even taken off their coat, but a few times I wish I’d been clearer about what I wanted much sooner. I dated a woman for over a month and we only made out once.

It was like we missed the moment to have a conversation about what we were pursuing: sex, a relationship, a sex friend who would feed my cats when I went on holiday. And so it kind of just drifted away. Ghosting has become a normal way to end things, I guess, but it did seem like if one of us had just come clean, we could at least be friends now.

Don’t Be Late

I’m an absurdly punctual person, and online dating has forced me to reshape my very nature. Everyone is late, all the time, always. Though my standards have fallen, I never went on a second date with someone whose sense of time was too crazy different from mine. All the tips above can’t make up for the biggest deciding factor of all — compatibility.

Somewhere out there is a person who will likely welcome a mate who shows up an hour late, because they’re late as hell, too! Chemistry, attraction, that special connection that makes you want to see someone again, can’t be artificially replicated. All you can do is get a lot of the nonsense out of the way so love has room to work its magic. Or so you can at least get to second base.

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