Hey Guys! This Is Tom: When Introducing Someone You're Dating Goes Awkwardly Wrong

I don’t know if I’m the only one who gets a surge of anxiety when introducing someone I’m dating to my friends — but it hits me every single time. Most of my friends think I’m dramatic for putting so much pressure on that moment, but I can’t help it. I genuinely care about everyone’s well-being and want harmony across the board.

Since I’ve never been especially close with my family, my friends are everything — they fill those emotional gaps and are often the first people I turn to when I need support. So yes, getting their stamp of approval on someone I’m seeing is super duper important.

A few months ago, a friend I used to date insisted on coming to visit me. I was hesitant — most of our conversations end in arguments — but because I’m annoyingly nice, I said yes. Coincidentally, one of my friends was having a birthday dinner that same weekend, and I didn’t want to miss it. So, I figured I’d just bring him along. Spoiler alert: I should’ve gone solo.

I picked him up from the train station. He practically leapt on me, and right then, I realized… OMG. I am so not into him like I used to be. I panicked a little inside but played it cool. I dropped him off at my apartment so I could finish up at work.

When I got back, he tried to kiss me again. Nope. I pushed him away gently, and we got ready for dinner. What I had forgotten — and this becomes important — is that he can’t hear out of one ear.

At the restaurant, I greeted everyone and waited for my best girlfriend, her husband, and another good friend to show up. Now, let me explain something: my best friend’s husband is very protective of me — think big brother vibes. When I introduce him to someone I’m dating, he usually doesn’t say much until he sees if they’re going to stick around. Smart man.

So we sit down… and “Tom” won’t stop talking. Like, at all. My friends try to ask him questions, but because of his hearing issue, he doesn’t catch them. Cue the awkward silence and confused glances.

I could feel the secondhand embarrassment radiating off my friends. I knew right then: I wasn’t going to live this night down. And spoiler again: I haven’t.

I’ll spare you the details of the rest of the night, but let’s just say I wasn’t exactly the kindest version of myself. It’s like my embarrassment turned into petty coldness. Not my proudest moment, but hey — sometimes your gut reaction is your loudest truth.

After that weekend, I made a new rule for myself: not everyone you’re dating needs to meet your friends right away. Sometimes, it’s better to give things time before merging worlds. If a guy’s not someone I can confidently bring around without stress, I’ll gladly sacrifice a couple nights out to avoid reliving The Tom Situation.

This One Time at Band Camp…

Yes, I went to band camp.
And no—nothing perverted happened there.
I was actually very innocent in high school.

But I’ve noticed something funny. Some stories from that time still make people laugh—even if I’ve told them a dozen times. And since writing my Bad Date series, I’ve gone on a few more dates.

What I didn’t expect?

Guys being scared I’d write about them.

Seriously. A few of them actually said:

“Please don’t blog about this.”

Let me clarify:

I would never write about someone unless there’s comedic relief involved.
If a date was sweet, sincere, and genuinely great? There’s no joke there—just sappy love content (which I enjoy on my own time, thank you very much).

One of my friends even told me:

“It’s not fair to the dating population—you basically wrote a ‘how-not-to-date-you’ guide.”

And they’re not wrong.

My blog is a bit of a blueprint.
It gives readers a glimpse into my personality, preferences, and the very real things that turn me off. But honestly? I don’t mind.

I consider myself an open book. If you want to know something—ask.
I’ve grown comfortable enough in my own skin that I’m no longer afraid of what someone might think about me.

So Here’s Your Friendly Disclaimer:

If you don’t want to end up as a headline in my blog:

• Don’t tip your server 5% after a $100 meal.

• Don’t pick Chick-fil-A for a first date when there are plenty of decent sit-down restaurants.

• Don’t show up at my place on a bicycle.

• And please, for the love of dating dignity—don’t be creepy. 😊

Simple, right?

Bad Date #1: Chick-fil-A at the Mall—You Can’t Make This Up

Welcome to the world of bad dates—a series where I let you in on some of my personal favorites. Luckily, I’m pretty laid-back, so I survived these with minimal emotional damage. But each one taught me a little something.

Let’s start with this gem from a few years ago...

I had just ended things with my ex-fiancé about a month and a half earlier. I was still navigating the weird emotional space between heartbreak and hopeful new beginnings. Then I went to a friend’s Super Bowl party. She was hyping up her husband’s best friend like he was the ideal man—great job, great personality, great on paper. She even said, “He’s someone I’d actually approve of.”

A week later, he and I were texting and made plans to go out.

He suggested we meet at the upscale mall nearby—the one with all the good dining options. We met up and he asked the classic question:

“Where do you want to eat?”

Now, I’m a little old-school. I like when the guy takes the lead, especially on a first date. Plus, I’m mindful of price ranges and don’t want to make anyone uncomfortable.

So I smiled and said, “Wherever you’d like.”

He looked around thoughtfully and said:

“Let’s do Chick-fil-A.”

I froze. Internally.

Chick-fil-A? On a first date? In a mall with places like Cheesecake Factory, PF Chang’s, Brio, and California Pizza Kitchen?

Don’t get me wrong—I love a spicy deluxe sandwich as much as the next girl. But this was giving food court energy, not date night energy.

I didn’t say anything. I’m not cruel, and I wasn’t going to make a scene. I ordered whatever I wanted off the menu. But mentally, I made a note:

“This is our first—and last—date.”

Thank God there wasn’t a dollar menu. I have a feeling he would've pointed to it and said, “Order from this side.”