Hello, Love
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Hello, Love

The Five Kinds of Guys I Met During my Fifty First Dates Experiment

Photo by Papaioannou Kostas from Unsplash

This morning I was messaging with a friend and his question made me laugh so hard I nearly fell out of bed. He wanted to know what kinds of men I’d encountered while doing my Fifty First Dates experiment.

That wasn’t the funny part.

What made me lose my balance, in a bed of all places, was that his question came from such an innocent and kind place. Were they, he asked, introverted, extraverted, confident, or shy?

I had never thought of it that way.

At all.

Instead, I gave him the true answer.

After fifty-one dates, every single one fell into one of five categories that were far less superficial than demeanor.

1. I’d like to have sex with you today, now if possible.

This guy is the one that most condemn, but he’s the most honest. If he wants to come to my apartment at nine o’clock at night, I’m under no illusion that it’s to get to know me better. If he only messages about sex on a dating app, he’s not being obtuse. A woman only has to make sure of one thing with this guy: not to make a hookup into anything more. If she does, he’ll say he was upfront, and she’ll slink away disappointed.

2. I’d like a sexual relationship with no commitments (because I already have commitments).

This guy is a little sneakier. Sometimes they’re upfront. One guy, I call, ‘Friends with Benefits’ in my Fifty First Dates memoir laid out his offer. He had moved back to Los Angeles to the apartment above his parents’ garage to care for them as they aged. He was also busy with an infant daughter whose mother lived eighty miles away.

But…he promised, he’d have the time to maintain a casual relationship on top of that. The same offer came from guys who worked in entertainment with a seventy-hour on-location weekly commitment. Guys who lived in New York City wanted a woman on call when they came to this coast. And of course, guys with wives. That last group was the most sketchy. They were careful to hide why they were so busy until they didn’t or couldn’t.

At least with these first two, it’s pretty easy to suss out their lack of commitment to a relationship. They’re seeking attention, not connection.

The remaining three, I’m still trying to wrap my head around. They say they want something deep, something real, but they haven’t reckoned with themselves quite yet.

3. I hate my life, my job, my apartment, and I’m hoping you can fix all that for me.

This guy thinks a relationship will fix his life. I met this guy at least half a dozen times. He always started with the fact that he was just moving even though he’d moved the year before. Half of them moved every two years, the other half, once a year.

They all hated their job. They were really the next Bill Gates or the next Steve Jobs or the next Quentin Tarantino, but the world had failed to recognize their brilliance. It’s why they were slaving away at jobs that were beneath them and that they could barely tolerate going to every day.

4. I can’t be alone with my thoughts.

This guy will text you and call you one thousand times a day. What do you think, they ask? Of every decision big or small. Yes, they’ve texted me to ask what kind of sweetener to buy, what kind of towels or dishes they should get (the ex took the last ones naturally). What kind of clothes to get. What to do with their overbearing mother and/or father. How to express themselves artistically. The list went on and on.

They have so many thoughts and would like to run each and every one by you. It’s said that the average human has six to twenty thousand thoughts a day. This guy will not keep the majority of them to himself. You will eventually google how to mute someone on your phone and use that newly acquired knowledge on him.

5. I don’t want to die alone.

This guy thinks he will die without a relationship. He wants someone by his side every day for everything. He’ll want to have breakfast together, and go to the gym together, and have lunch together, and take a walk together, and take a shower together, and nap together, and have dinner together. You’ll have to go to bed and fall asleep at exactly the same time. He’ll talk about how he wants to have you by his side from now until he exhales his last breath. You will have to tell him the truth and ruin the ending.

Spoiler alert: We all die alone.

Jolie Moore is a romance author and the host of the podcast Fifty First Dates. You can subscribe to her weekly newsletter here.



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Jolie Moore

Jolie Moore

I write crazy, beautiful love stories because I believe storytelling is magic. Join me as I try to find my Mr. Right or maybe Mr. Right Now.