Things You Shouldn’t Say on a First Date

A (Mostly) Fictional Story

I waited at the front of the restaurant with a mixture of nervousness and anticipation, the norm for a first Internet dates. Online dating is tough; you never know when it’s time to meet up in person and it’s impossible to get a read on what someone is actually like in real life. They can edit an email as many times as they want as they strain for literary perfection, but in real life, there is no backspace. Once you say it, it’s on the table, it’s out there, it has been said.

I check my watch. He’s late, but only by a minute or two. A man is walking towards the restaurant, and for a fleeting moment my heart skips as I wonder if it’s him. Another risk of online dating: you never know how old the photograph is, how much it’s been doctored, or if it’s really the person you’re speaking to. I relax as he passes me when a finger taps my shoulder from behind, startling me. I turn quickly with a twinge of anger.

“Jessica? Hi. I’m Nate.”

He offers me his hand, and I take it, feeling a small tremble in mine and sweat in his. Gross.

“Shall we?”

We enter, we’re seated, our drinks are in front of us and we’re perusing the menu. He basically begged me to go on this date so I decide to order what I want instead of what I would normally do on a first date, which is skimp. I had qualms about meeting him. He lives in his uncle’s basement. He works in retail but hasn’t said where. His personality seems wishy-washy.

The waiter approaches and breaks the awkward silence. “Are you ready to order?”

I look at him, he nods, so I order. “I’ll have the filet as is.”

He looks at me. “Wow, really? Don’t you want a salad or something instead?”

He gets a nasty glare from both me AND the waiter.

“Yup. I’m good.” Now I’m ordering dessert, too.

“And you, sir?” the waiter asks in a sarcastic tone.

“I’ll have the crab cakes. Can you put onions on them?”

Well, at least I won’t have to kiss him now. Thank God.

The waiter nods, takes our menus and leaves us in a sea of silence. I have nothing to say to him, especially after that little comment. I’m still not sure if it was about my weight or the money, but either way, I’m not impressed.

“So, you like music?” he asks.

Here’s the biggest problem with going out to dinner for a first meet up through an online dating website: there’s a TON of down time, which is great if things are going well, but can be the most painful time EVER when the guy is a dud.

“Um…who doesn’t like music?”

“Yeah, true. I like it.”

Awkward silence.

“So how old are you again?”

Another no-no in my book. It reads as You look older than you claimed on your profile…are you a liar?

“I’m 35. You?”

“32. No kids?”


“Aren’t you worried?”

I can’t believe this guy. “About what?”

“Well, you’re running out of time, you know? To have kids?”

I’m surprised I can hear his voice over the sound of my biological clock ticking.

“Oh, my gynecologist says I still have a few good years left in me.”

He doesn’t notice my sarcasm.

“Well that’s good I guess. When do you want to get married?”

Who asks things like this on a first date?!?

“Well I have a date set for next Saturday at my church, just in case.”

He shifts in his seat. Fixes his collar. Looks back at me.

“What do you mean?”

“I was kidding.”

“Oh. You’re funny, huh?”

“That’s what they tell me.”

Awkward silence again. I feel like he’s waiting for me to say something funny. I don’t really know any jokes, so I take a sip of my wine, then another, then another. Then one more.

“So…” he says. I look at him with minimal expectation, but he just twirls his wine glass. “I hear this place is pretty good.”

“Yeah, this is where I go for all of my Internet dates. I’m working my way through the menu, then I’m switching restaurants.” I say it with such a straight face that he nods.

I look at food coming, but it’s not ours. This is excruciating. My friend scolded me for meeting people in restaurants. He said anything involving waiting for food in a busy restaurant could be a recipe for disaster. I’m starting to think he was right. But it’s too late, I’m in for the long haul now.

“Oh crap!” he says, ripping me from my train of thought, which happens to be possible excuses I could use to run out on him. He’s looking over my shoulder so I turn to see what has caught his attention.

“Don’t look! What the heck!” he yells at me. I mean it too, yells. I look back at him. “Oh never mind. I thought it was my ex.”

I stare at him.

“She was crazy.”

I still look.

“Is. Is crazy.”

I decide to say nothing and let him continue.

“She keeps texting me crazy things. Yelling at me for things I did two years ago. Or saying dirty things. Or sending me…pictures.”

Dirty pictures, he means.

“When did you two break up?”

“Last month.”

I think about today’s date. It’s the eleventh. So this guy may have had a girlfriend as recently as twelve days ago.

The food comes. Thank God.

“Filet and” he gives me my food, “…crab cakes for you,” he practically spits out.

“Could I get another…” the waiter is either legitimately too far away to hear him already or he downright ignores him. Nate puts the mostly empty wine glass down.

“So what about you? Any crazy exes?”

I shove a giant piece of steak into my mouth so I don’t have to answer. It’s none of his goddamn business what mistakes I have made.

“Wow…slow down fatty.”

I almost choke. I am maybe five pounds overweight at that, and I guess it’s a joke. But this guy is either seriously awkward or a huge asshole. I swallow the food and take a smaller, more sensible bite.

“Can I take your picture?” he asks, taking out his phone. I almost choke again.

“I’d rather not.”

“It’s just, you looked cuter in your profile. I mean, you know, you’re beautiful! I just thought maybe you had Photoshop or something.”

This has to stop. I need to scare him away now before it’s too late.

“I’m in rehab!” I blurt out. It’s a lie, of course, but worth a try.

He looks at me.

“Me too! What for?”

“Um…” my brain stumbles over his confession and my lie. “…I drink. I drink waaaay too much.”

“Oh. For me it’s drugs.”

I take another bite. He waits for me to start more conversation.

“Excuse me,” I say, grabbing my purse.

“What, you gotta pee NOW?”


I walk in the direction of the bathroom and then, once out of his line of sight, run for the exit.

8 responses to “Things You Shouldn’t Say on a First Date

  1. Great story! I’d love to know what parts were fictional; hopefully most of the things Nate said.

  2. Wow. Just Wow. This is a most horrific and fabulous story.

  3. Good story. And it’s all about the word “mostly,” isn’t it?

  4. I’ve been on that date. Except I did order a salad. You seriously need to quit following me around. 😉

    Great work as always.


  5. Don’t help out people who are going to say awful and stupid things on a first date. Just let them be terrible so you can more efficiently weed them out.

    That said, this was a hilarious story and I am sorry for you.

  6. Hahaha I truly LOVE this story. It’s written very visually. I see the whole scene very very clearly. Thank god I’ve never had that bad experience before. Excellent work Den!! 🙂

  7. Oh my word I have been there!!!! This was hilarious. And sadly realistic 😛

  8. I’ve been on way too many of those. At least I’m not the only one. :-/

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