Dating mistakes I’ve made so you don’t have to

I really, really, don’t like to call myself a “dating expert”. That’s not to say that I disagree with the idea that there are experts when it comes to dating, relationships, sex, and anything else that falls broadly into how humans partner with people, I just don’t think I’m one. What I know is that I’m experienced.

That experience is what I think makes me, not an expert, but a qualified voice to offer dating and relationship advice. I’m not always right, and I don’t think what I have to say is the end all be all when it comes to dating and relationships, but I know where my opinions come from.


Lots and lots of dating mistakes. Like, too many to count, and more often than you think. It all worked out in the end of course, but all the mistakes I made inform how I’ve dated in the past, and what sort of advice I give.

So let’s talk about some dating mistakes I’ve made so you don’t have to:

Spending way too much on first dates

When I was younger, how I differentiated between dates when I was broke and “real dates” was dollars spent. At some point I started to qualify whether or not something was a real date by how much money I spent on that date. When I was young and broke a date with me probably involved a ton of walking, making out in public parks, and trying to find cheap/free things to do. Once I grew up that changed to an extent. The mistake I made was overcompensation, by spending too much on first dates. I went from spending $20, max, on first dates by finagling free drinks to dropping 20% of my  two weeks pay on a single first date. (Seriously, god bless NYC gallery openings, and any other open bar deal I found in the early to mid 2000s,  if not for you I’d never had been able to date in NYC)

Now, “too much” is relative of course. If you’re a millionaire, spending $200 on a date is nowhere near too much for you, but if you earn minimum wage, that might be too much for you.  I’m all for splurging when you can, but I could not afford to spend 20% of a paycheck on a single date with someone I didn’t even know if I liked.

My advice to you is to never spend “too much” on first dates, whatever “too much” means to you. If that means putting dating into your budget, there’s nothing wrong with that. Not every date needs to be expensive, or even cost a cent.

Trying too hard to impress someone

Here’s a very specific, very silly, and very thirsty mistake I made that had little to do with money, and more to do with too much effort too soon for a stranger. Mind you, it wasn’t even a date.

I met a woman who, in passing, mentioned that she liked a very specific bagel place. At most she mentioned that she used to live near that place and subsisted on these bagels for years. Foolhardy, and ever ready to go above and beyond to impress a pretty woman, I planned to meet her on her break from work and bring her a bagel. Cute right? On its own, maybe, but let’s add some layers to confirm how thirsty and over the top I was being. For starters, the bagel place was in Brooklyn, fairly close to me, but inconvenient to get to. Next, she didn’t work anywhere near Brooklyn, she worked in Times Square, where dreams go to die. Third, who wants a cold, surprise bagel it took 30 minutes to deliver? Nobody that’s who. I delivered that bagel and never saw or heard from her again. With good reason I might add, she really dodged a thirsty-ass bullet in my opinion.

It didn’t cost much, and it was mildly inconvenient, but whatever. The issue was, it was just too much effort for someone who wasn’t all that interested in me romantically. That I think, is the bigger mistake. It’s one thing to try your hardest to present the best version of yourself, it’s a whole other thing to go above and beyond for someone you’ve never met. The amount of effort you should put into impressing someone before a first date, or in the early stages of dating, should be at the “job interview” level. Best foot forward, but don’t show up to your interview (or first date) in a tuxedo. You get me?


Conducting a bit of online research on someone before a first date is a good idea in general, because people are strange and potentially dangerous. The mistake I made would be over-researching. I’m guilty of conducting internet research that escalated from assessing risk to full-on private detective work. I’d never found anything too bad about someone before a first date, but I did learn things that made me lose enthusiasm for a date, or things that made it hard to have normal first date small talk.

If you’ve already stalked someone’s Facebook, and learned where they went to school, what they do for a living how many siblings they have, that they played clarinet and high school, and so on, I can promise you that it can be very awkward to try to have a normal conversation. Learn from my mistakes and do just enough searching so you avoid a date with a career criminal, but not so much that you run out of things to talk about because you already know them.

Being too accommodating

What’s the biggest way you’ve inconvenienced yourself for a first date? Mine was traveling almost 2 hours for a “date” where I helped a woman shoot a student film with her friends. I kid you not, I traveled almost 2 hours (then had to travel 2 hours back home), on a Saturday, to meet a woman for our first date knowing that our date would also double as her finishing up some weird MFA project she had going on. Now, this situation is obviously very specific, so here are the mistakes I made in general terms:

  • I traveled completely out of my way for a date. Didn’t meet half way, a quarter of the way, we met all the way in her neighborhood because I was accommodating her.
  • Our first date wasn’t a date, so much as a hang out with friends, and I HATE group dates with strangers.

Now, my version of being overly accommodating might be different from yours, so here’s a good way to tell to see if you’re too accommodating: Ask yourself, how much inconvenience you’re taking on for a date compared to the person you’re seeing. If you’re taking on 100% of the inconvenience of a date just to go on a date with someone, you’re doing it wrong.

Going on dates just because

Have you ever agreed to a date you had no interest in? Maybe there’s a teeny, tiny chance that you’ll have a good time but in my experience, where my mistake lied, was in counting on an unlikely eventuality. There’s always the off-chance that you can meet someone when you least expect it, but you can’t brute-force things like chance.

It’s one thing to continue dating when you’ve become disheartened, it’s another to go on a date knowing you don’t like the person and don’t enjoy the date idea, in the hopes that through some miracle, you’ll have a good time. By all means, date through disappointment, but that doesn’t mean going on a date with just anyone. It’s natural to get a bit down on dating, it happens to the best of us. What you should avoid doing is going on a date where you know you won’t enjoy yourself.

If nothing else, I hope you learn from my mistakes. I’ve made plenty in the hopes that you won’t have to.

Good Luck Out There.

Also published on Medium.

2 Replies to “Dating mistakes I’ve made so you don’t have to”

  1. My coworker is a 25 yr old single male and we got to talking about dating and he mentioned how expensive it is to go on all those first dates — expensive dinners in the city, cocktails, etc. I reminded him that he did NOT need to be doing that, and something simple like coffee or ONE drink would suffice, especially if he wasn’t totally sure about the girl. No one should be dropping that kinda money on every date! Great post 🙂