Everything I Learned From Going Out With A Serial Celeb-Dater

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We met on Bumble. Just like the love stories of old time.

I remember being surprised the conversation had gone well because, frankly, I’m absolutely awful at dating apps. Instead of dropping slick one-liners and hoping to lock in second base in a single text, I’d decided a long time ago to always make the most terrible joke I could think of on the spot and let the chips fall where they may. Because if you don’t appreciate pun-based humor, our first date isn’t going to go well anyway.

But the extremely pretty girl who swiped right actually enjoyed my mashing together of her name and "coconut" — it worked in context — and in no time at all I had a date for Thursday after work.

We met at a quiet bar and, for the first time in the history of online dating, she was actually cuter than her pictures. What’s more, she was a hardcore football fan, drank whiskey, and could quote Rocky. It was like I’d designed her in a lab.

The two of us sat, chatted, and drank for the better part of two hours before deciding to venture elsewhere for something to eat. As we were paying the tab, a song by a moderately-popular band called Atlas Genius came on the bar’s speakers. I casually said, “I love these guys.”

“Oh, we should call the lead singer and tell him!”

Wait. What the what?

She immediately pulls out her phone, scrolls through her contacts for a few seconds, then puts the device to her ear. “Hey, I’m with a friend and he loves you guys! Yea… here, take it,” she said as she handed me the phone.

I genuinely don’t remember what happened for the next fifteen seconds; the guy was polite, I said something lame, then we laughed about how crazy this girl was for calling him out of the blue like this and I handed her the phone back. The details are hazy because my brain was far more concerned with how the hell this girl casually had the lead singer’s number and was comfortable enough to call him out of the blue, not to mention, know that he'd answer.

Curiosity and whiskey got the best of me at the next bar, and I finally asked the question that’d been bugging me for an hour. She laughed and half-brushed it off by saying, “Those guys used to open for my ex.”

More WTF. Because like I explained, "those guys" are not a small act. So whomever they’re opening for has to be a big, big act.

My poker face didn’t hold, so she did a half-embarrassed laugh and said, “I don’t want to talk about it.” But after two more bars, several whiskies and incessant pestering by yours truly, she finally fessed up: her ex-boyfriend is in Imagine Dragons.

I’m a pretty confident guy, but that might be the most emasculating moment of my adult dating life. I know money and status doesn’t matter in the fairy tales, but this was LA; we were literally in a bar on Sunset Blvd. at the moment of that reveal. I’m very happy with my life as a writer, but in that moment every screaming insecurity that usually sits dormant in the dark recesses of my gray matter just came stomping back up to the surface. How am I supposed to measure up to the internationally touring, wildly rich musician that, I’d find out later, she only just split up with weeks before?

Fortunately, I had enough liquid courage pumping through my veins to not derail the evening. The night went on far too long and we had a great time, but when I got to work the next morning — considerably later than normal — I looked and smelled like a bridge troll who’d been hit with a dumpster full of liquor and diapers.

Naturally, my coworkers asked what happened, and I told them the tale just as I told it to you now. This caused an obnoxious amount of laughter and, for the rest of the day, every time I stood up and went to the bathroom, they’d play "Radioactive" over their computer speakers.

[Editor's note: I can fully attest to this, and it's still absolutely HILARIOUS.]

In the midst of all this, I was texting back and forth with the girl, assuring her that I too had a great time and that we should definitely do it again — as soon as the hangovers passed. We agreed on Saturday afternoon.

We met and picked up right where we left off. The banter was fun, drinks were had, and she wasn’t half bad at darts while she was sober-ish. Again, everything’s going great, so I felt comfortable bringing up what had happened at work the day before.

She laughed and responded, “Well, I definitely shouldn’t tell you about my other exes then.”

Son of a...

“Then you shouldn’t have said that,” I replied, which led to another lengthy session of pestering before she finally fessed up to her star-studded list of former flings; there were definitely a few more notables than this over the course of 6+ years, but the highlights were one of the main guys from True Blood (I'd never watched it, so the guy’s name didn’t stick), Adrian Grenier of Entourage fame for a couple years (definitely watched that and knew who he was) and Leo. Yea, that Leo, for a couple weeks a few years prior.

My first thought was that I absolutely couldn’t tell the guys at work about this.

Then, I sort of just shook my head and chuckled over the bar for several seconds. I can’t imagine many other men would have handled the situation with more composure. It’s not a regular occurrence for your date to tell you (very humbly and with a sense of embarrassment, I should point out) that virtually all of her exes in recent years are A-list Hollywood stars.

I forced a laugh, ordered a shot, told her she’s insane and picked up our darts game. Because when you’re out with a beautiful, cool AF girl and everything seems to be going great, you’re don’t let their previous dating history stop you. Doesn’t matter if her ex is the local mechanic or George Clooney.

I’m glad I did. We ended up dating for another couple happy months before calling it off for a reason completely unrelated to this story — long story short, somebody moved, and it fizzled out. So in no way did her history affect the decision to split.

But I’d be lying if it wasn’t on my mind… not constantly, but definitely every now and then. I got over that initial wave of inferiority easily enough, because she gave me no reason to dwell on it. It was clear that, in this case, I wasn’t being constantly compared to the men of her past — I’d had that relationship before, I knew the signs, and this wasn’t that.

It was more of a subconscious (and possibly unfair) judgment on my end. Because if for several years you blanket-date celebrities, what does that say about you as a person? I’m no shrink, I don’t even know where to start breaking the psychology of that down, but I definitely let it occasionally, in little ways, affect me. And not for the better.

A year or so after I’d broken up with the girl, I was telling a buddy this story and he very candidly exclaimed, “I could never have f***ing done that, man. You know where she had been? What she was used to?”

“Thanks for the vote of confidence,” I replied. But he’s not wrong. No matter how cool she was about not bringing up her star-studded past, that little voice in the back of my head never really shut up. There’s no way around it, and it’s true in any relationship — it was just magnified times eleventy here. And on top of that, there were my half-baked Freudian inferences about her personality and character based on her obscenely prestigious dating rap sheet.

Like I said, we ended things before any of this came to a head. But sometimes looking back on it I wonder, if everything else was great and the relationship was going somewhere serious, would I have been able to accept her dating history?

I honestly don’t know.