nice guys courting

A Tale: One Time I Intentionally Tried to Date “Nice Guys” and Failed

Recently I was relaying to one of my current besties some dating tales of old. This particular tale was of a time that I signed up for dating “nice guys.”

Mid-twenties. I allowed some best friends of mine to set me up with one of their single male friends because I had finally tossed my hands up in the air and decided I couldn’t do this on my own. I clearly was choosing all the wrong people: entirely too dependent; too emotionally unaware; too unconfident about themselves to be confident about who I was. Some combination of those.

I want to say that it was a lot to relinquish the control of my romantic life over to friends, but it wasn’t. The level of face-palming and eye-rolling at my own blubbering through romance had reached its peak. The heartbreaker merry-go-round ride (doesn’t that sound like the worst carnival ride ever?) had become very old and entirely too cyclical – as merry-go-rounds are, obviously.

This is a perfect metaphor actually. Rides that go in a constant circle make me seriously motion-sick.

nice guys boring like merry-go-rounds

A roller coaster that dips and climbs, weaves, and loops: I’m there. Give me a fast, round-and-around-again ride (the Teacups, Swings) and I’ll be lucky if I’m not tossing chunks into the closest trash can. The Ferris Wheel and Merry-go-Round I can handle because it’s a slow circle, but even then, they just keep going in the same direction. You get bored eventually and start to wonder when can you get off.

There you have it. My love life described by carnival-metaphor.

So here I was, the only one still single among both high school and college friends, and finally stepping off another irritating, disappointing, predictable heartbreaker merry-go-round. I was tossing my hands up in the air to my friends, a couple who had been together since high school. They wanted to set me up with nice guys. Guys they knew and could attest were decent people and motivated, balanced, and from good families.

Put like this, nice guys sounded pretty damn good. I was pretty done with “bad boys” anyway.

Not that I ever intended to be with “bad boys.” It just kind of seemed to always happen. They never seemed dependent, emotionally stupid, unconfident, controlling, manipulative, possessive, or crazy in the beginning. These guys I dated were sneaky little fuckers. Charismatic and charming, appearing confident and in-tune in the beginning. Then like a pot of water sitting on the heat too long, they boiled. Or maybe a lobster being put in the hot water is more accurate; their shells turning color as the pressure rose. Pick whichever one you want. The point is, somewhere along the way they transformed.

So, I signed up for nice guys. As luck would have it, my friends knew someone they adored who was also single. (*Applause!)

nice guys fancy guys

Single and going after a J.D. (More applause.)

Hardworking and motivated. (More applause.)

Independent and confident. (Can I get an Amen?)

From a good family… (Halelujiah!)

… with wealth.  (Praise Jesus! My inevitable problems as a soon-to-be poor and hapless writer would be solved if we got married!)

Just kidding about everything in that last parenthesis. I was not planning our wedding and having a lot of money has never been a requirement for me.

Like most things “on paper,” the deal looked good. I agreed to meet Nice Guy by way of us all going out on a double date. In my mind, it would mean we each would be less nervous knowing a mutual party. The date was set. They made dinner reservations. They came up with the plan. All I had to do was show up.

Now, I know that you can feel the tension I’m building here so before you get too caught up in your own theory that I didn’t show up, I would like to tell you that I did. I showed up. But as soon as I showed up and began to get more information on Sir Nice Guy, I regretted my decision to give this a try.

He was conservative. (Buzzer!)

He dressed in J. Crew. (Ick!)

He was the Third. As in FirstName LastName the Third. (Aristocracy!)

This was not going to be a good match. And now I would have to suffer through this date with witnesses. I would have to eventually tell my friends this wasn’t going to work. And they may hate me. Why, oh why, did I agree to sign up for nice guys?!

Yes, clearly I was judging a lot before even knowing him. Notice how the title of this post includes that I failed.

I started taking shots, if for no other reason than to just make me feel a little less focused on how terrible I thought it would all go. To drown out those ill-placed judging thoughts. I wanted to give this guy a chance. They had said he was nice and hardworking and all those other great things. Certainly, I could overlook two of the three new pieces of information. (You can decide which one was a deal breaker and not to be overlooked. Feel free to leave your guess in the comments.)

nice guys make me want to do shots

Shot after shot I tried to calm my liberal-minded, jeans-wearing, less-than-upper-class ass from derailing the night my best friends had worked so hard to coordinate and were so excited to see happen.

Yes, I’m so much a people pleaser that I didn’t want to ruin their orchestrated love-affair between me and Nice Guy by being sober and potentially rude, so I got tipsy instead. Cause I’m classy.

Really tipsy. Like far too tipsy to be meeting someone new and needing to make a halfway-decent first impression. Far too tipsy to give the first guy in their lineup of nice guys a genuine chance. Depending on how you look at “genuine” in this context.

Nice Guy arrived. He was cute. He was polite. I wanted to like him instantly. But he wasn’t my type. Not in the “but my type is the wrong type” kind of way. I knew my type had been all kinds of wrong. (Go back up and re-read the part about bad boys.) But this was more from the lack of chemistry type. The, I’m not attracted to him, type. The, if people saw us walking down the street holding hands they’d be like “They’re an odd couple,” kind of type.

We were going to a Mexican restaurant down the street. It was hot out. Three of us were in jeans. One of us was in khakis. Three of us were in sandals. One of us was in loafers with tassels. Two of us were in tank tops, one of us a Polo, and one of us in a business shirt and blazer.

I wanted to like him. Really. Who didn’t want to end up with a nice guy?

Me, I guess. Cause I judged him instantly like the terrible person I am. He was not “my people.”

Another shot for the road and I giggled the entire way to the restaurant, slightly weaving along the sidewalk, accidentally bumping into him (shoulder-to-shoulder) which, of course, seemed like girlish flirting. And my liquor-induced giggling and shot-heightened personality meant much of the same throughout dinner. He was smitten with me by the time we were through our first round of Margaritas.


Nice guys like me as much as bad boys.

I shouldn’t have been so disappointed.

We went back to our friends’ place after dinner. We hung out watching episodes of The Office, a show they all loved. I was still drunk, so anything was funny. Things were blurry and sideways and looking better than they had. Don’t get too excited. Things got weird and even me in my drunk state knew it. My friends dismissed themselves to bed. They left me and Nice Guy alone. And from there I thwarted awkward cuddling and hand holding and absolutely, positively and firmly turned down the offered foot rub.

I. Don’t. Do. Feet. Mine. Or others. I don’t even like pedicures. Everyone who knows me can attest to this. The only exception is babies and my son. And even his feet will have a shelf-life.

Somehow I made it known I was tired and nothing would be happening. And I’m fairly certain there was not even a kiss on the cheek, but I honestly can’t say with 100% certainty that is the truth. But I do know he left. I passed out on the couch. And was both relieved and worried the next day when I woke up and didn’t remember all the details. So I had to rely on my friends.

nice guys and hangovers

Had I been kind? Yes.

Had I been too kind and it looked like flirting? Yes.

Did I appear drunk? Kind of.

Did I say anything stupid? No.

Have you heard from him yet today? Yes. He’s super into you.


And so began a several-month stint of giving Nice Guy chances because I just so desperately wanted to be a normal person who liked other normal, nice people, especially normal, nice people that my friends actually approved of and didn’t look at me all like, “Seriously? You chose that guy?”

I also figured maybe the dynamic would be different if:

  1. My friends weren’t present
  2. I wasn’t present drunk
  3. He eased up and dressed a little more casually (Maybe he had dressed up for the first “date” in order to impress and the next would be different.)

But Nice Guy as nice as he was, just didn’t know how to relax and be himself. And the real him I would have been interested to know or meet.

When we went out the next time for dinner, it was purposefully having Sinatra playing in the car and serenading me on the way to the restaurant- specifically emphasizing the most romantic lines; it was asking the waiter for the bottle of the finest wine; it was constant references to money, wealth, the family business and the boat.

Though at least the first half of those things were well-intended, gentlemanly gestures of courtship, they didn’t feel natural. At least not to me, the recipient. They felt forced. Like he had read a manual from the 50s. Or his moves were taken out of a rom-com and applied to real life and somehow the magic fell flat – probably because the chemistry wasn’t there to begin with.

nice guys courting

I hated myself. I’m an old soul and I love Frank, so why didn’t it work? Certainly, I wanted to be romanced, but none of this was working. Was it because he was one of the nice guys and I didn’t know what to do with that? Or was he just not the guy for me?

Clearly, it was me. He was perfect. And I was a perfect mess who had been with all the wrong people for so long, I wouldn’t know what the “right one” would look like if it showed up in its BWM and bit me.

And so over a handful of months me and Nice Guy communicated and lightly texted and occasionally got together until finally, it fizzled out. I don’t remember saying anything specific to him. As in, I don’t remember offering a “This isn’t working” or “It’s not you, it’s me,” even though I was pretty sure it was in all actuality.

Once it fizzled, I called off the search. I told my friends no more set-ups. Partially because I couldn’t handle the feeling of failure when their choices didn’t work out and I had to explain it to them. Which sounded kind of like, “So, I suck. Sorry.”  Partially because I wasn’t convinced I could handle one of the “nice guys,” at least not if they were all hanging out at the same Country Club.

I hung up my hat on intentionally dating nice guys. Mostly because I didn’t feel like I deserved one.

Obviously, I hoped that whomever I ended up with would also be “nice” at least in all the best senses of that very flat, unexciting adjective. But I wasn’t going to start off my profile by saying I was looking for a “nice gu.y”

Eventually, Nice Guy faded into a distant memory until I nearly forget that dating experience altogether. All until something triggered a flashback to the night with margaritas, and the khakis, and the foot rub and I found myself relaying this very story to a friend.

“You really are a heartbreaker,” he laughed while feeling genuinely sorry for Nice Guy.

Sigh. I know. 

“Sounds like he was one of the nice ones.”

Louder sigh.

He sure was. But nice wasn’t enough. Not for me then. Because I had seen myself as a “bad girl” and they don’t deserve nice guys.

letter to a nice guy

So, Nice Guy, wherever you are, it really wasn’t about you. And I hope that you are still wearing khakis and blazers. I hope you’re still holding open doors and serenading some lovely person Sinatra songs and they are loving every minute of it. I hope you’ve found your Nice counterpart, your equal. And in having done so, it proves you were perfect just as you were but just not perfect for me. Also. Please don’t hate me for writing this post. Clearly, I was the messed up one. And not very nice at all.


*This is the first post in a 3-part series Dating Nice Guys. 

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