11 Stupid Things Men Said to Me on First Dates

by Jessica Ashley
Originally Published: 
A couple on a first date having drinks, woman disinterested because the man said something stupid

There was a time when I was dating a lot. Going on lots of dates with lots of men. And none of them were dates with Matthew McConaughey.

It was a great, manic, empowering, rather lonely time. Mostly, it was part of the process of widening my world post-divorce, of trying on different parts of my personality and also interacting with adults IRL over conversations that had nothing to do with which preschooler pees on the cots during nap time. Or Star Wars. Or a thousand questions about boogers.

But that doesn’t mean there were not some pretty inane things said on those dates. (I’d use the word “juvenile,” but honestly, my then-4-year-old kid would never think of saying such insulting or awkward things to another person in the middle of analyzing something-something-Tauntaun.) Sure, there were hot guys and crazy-smart men and delicious gents and those with fascinating stories. There were schmoozers and wordsmiths and a few who could look at me and persuade me they were … well, Matthew McConaughey. But the standouts are really the men who let some really damn dumb stuff fall out of their mouths.

“Did you really say that out loud?” I found myself saying on repeat. And the real winners thought that was more funny than embarrassing. Here are some of the top offenders:

1. ‘Wow! You look better in person than in your profile picture!’

Hey, there, no need to express all that excitement that I am far less of an ugmo in person, Guy Wearing a Cat-Hair-Covered Fleece and Ill-Fitting Khakis! And since he was the person who pursued me, pressing the dating site’s equivalent of a thumbs-up on picture after picture on my profile, should I take that as meaning I met his very low standards or that he was crossing fingers I’d outdo my carefully curated collection of just-enough cleavage shots, pictures to prove I have friends and travel and also have an amazing personality? It didn’t matter because, honestly, he looked far schlumpier than his better-days profile pictures, and this was only the beginning of a very bad onetime date.

2. ‘All my exes are crazy. Like, psychopaths-who-need-medication crazy.’

Gentlemen of the dating world: Women never, ever believe this. Why? Because we are counted as someone’s crazy ex pretty much every day of our lives. Also, if you are the common denominator for all that crazy, then clearly you get the big, shining crazy crown. This was said moments after Cat-Hair Fleece Guy was startled by my in-person beauty.

3. ‘I really feel like you are too needy to go out with again.’

For those of you keeping score, this is the third (but not final) offense for Cat-Hair Fleece Guy. I’m sure it won’t surprise you that I spent most of the date sipping my PBR (thanks for ordering for me, sir) and listening to him reveal detail after detail about his exes. After an hour (or 15 minutes—who knows?) of too much and too long, I smiled and said the thing about considering who the common denominator in all those Nutters McGee relationships was. That’s when he forked over the two bucks for our beers and hit me with this needy line.

4. ‘Should we connect on LinkedIn?’

Adventures in Cat-Hair Crazy Guy came to a complete halt moments after he enlightened me with how needy I am, but four years later, his profile pic popped up again in my life—this time on LinkedIn. Nothing says, “We really shared a time way back in those nostalgic days, didn’t we, doll?” like, LinkedIn, huh? He clearly didn’t remember me and my less-than-acceptable photo collection or truths spilled over PBR when he tried multiple times to connect on the social network. An “OH. HELL. NAW.” reply sent the cat man away for good.

5. ‘How do you feel about pain?’

This was another man who—coincidentally?—enjoys pressing “add friend” on my social profiles years and years after he gruffly whisper-spit this question into my ear. We were in my car, and I suppose this was his way of inviting me up to his apartment? It was pre-Fifty Shades of Grey, so he didn’t even have the excuse of the incessant movie trailer to persuade him to try it out on a lady. I declined—to ever see him again. The fact that he’d forgotten his wallet (twice) was painful enough.

6. ‘How do you feel about men with lots of hair? Everywhere?’

If you have a good reply to this question, I invite you to insert it now. Just go ahead and say it aloud to your screen. Perhaps somewhere, at a wine bar ordering an off-the-menu blend, this guy will get the message. (And, no, he said it does not mean he also fully embraces a non-waxing lady.)

7. ‘Are you going to write about me on your blog?’

The answer to that is simple: Nope. I am going to write about you on a site where many, many more women will take it as a cautionary tale that dating is ridiculous, hilarious and irritating as hell. But worry not. I’m also going to tell those same women that it is worth getting past all of you narcissists to spend some time with some really great people and maybe even feel a spark grow into a big love.

8. ‘When can I meet your son?’

Also a simple response: Neverevereverever. At the time, I had a young child and kept my dating life compartmentalized. He didn’t need to know I was Match-Dot-Harmony-PlentyofFish-ing it, while he was at Dave & Busters with his dad. My single-parenting style said it would have been totally inappropriate for him to meet every yahoo I’d shared avocado bruschetta with one time. If I needed to explain why I’d be waiting a very long time and already in a deeply committed relationship with a fan-freaking-tastic man before I made boyfriend-kid introductions, then there was really no need for a second date. Or even an answer to this one. Well, other than, “As soon as I can meet your mom, ex-wife, boss, other-Tinder-ladies you’re meeting up with this weekend.” #squirm

9. ‘You wear a lot of makeup.’

And you have on a velvet blazer, friend. If first dates are for pointing out the obvious, then I guess those are both perfectly acceptable things to say. The subtext, which might just be third-date conversation, is that I’ll get vulnerable and show my flaws to an interesting person when I am comfortable and ready. Until then, seven layers of concealer it is!

10. ‘I’ve never met a woman who wasn’t looking to get married. Why are you dating then?’

Oh, darling, darling, darling. We didn’t meet at a cotillion presented by the Betty Draper School of Snagging a Fine Man. Women these days do crazy things like burn bras and take care of themselves financially. We can choose to live in sin and have children out of wedlock and want to have delicious sex and deep conversation and adventurous companionship without legal commitment. Gloria Steinem said so, and I am sticking with her on this one. I think, if Betty were still around, she might even side with us, too. Next in line?

11. ‘Let’s connect on Facebook!’

How about we wait to see how good of a kisser you are? Or maybe if you proclaim you’re “fiscally conservative” (code for Republican) or “newly divorced” (code for thinking of filing) or “late for a work thing” (code for on your way to date No. 3 of the evening). I had a strict ten-date rule for accepting FB friendship with men I dated, because there is just no need for all those strangers to poke around in my whereabouts and pictures and kitty-cat-video links with all of the other strangers I’m already friends with there. This worked out well, particularly when I had to nix a second date, or was stood up, or was told I’m needy for wearing so much concealer. Because if you think the kooky first dates get upset if you don’t want to go out with them a second time, then just see how they react when they realize you’ve unfriended them after an awkward hour spent with nonfat lattes. Best to just lock down your social from the start.

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