When A One-Night Stand Turned Into A Boyfriend

You can learn a lot from a one-night-stand.

I am out with friends from church—yes, church—when I see him across the room, laughing with his friends (two couples) and wearing a Tommy Bahama-type shirt donned with pineapples that makes it look like he’s been on the beach in Hawaii, not L.A. He catches me watching him, and I return my eyes to my friends. He looks familiar and I realize I saw him at a volunteer event a few months prior, where people in their 20s and 30s help tutor kids after school. I’m smitten.

A few minutes later, around 11pm, my friends want to call it a night, but after a 70-hour work week, I don’t. This is my one night of freedom. They can’t leave, which means I’d have to leave, too. I can’t stay at a popular L.A. bar alone on a Friday night.

I look at Mr. Hawaii again, hoping to send him a telepathic signal. I feel he glances at me for a second, but then nothing. I follow my friends out the door.

“Leaving?” a voice says. I turn. It’s him.

“Afraid so, they want to go,” I say.

“Funny, my friends want to split, too. But I don’t. Want to stay?”

I look at my friends, who mouth, “Will you be OK?” I tell Mr. Hawaii I’ll be right back and go confer with my friends outside. I explain how I actually saw “the guy” at an event once and, even though we never officially met, it was for a good cause. “Of course you have to stay!” says my friend Kate. After my breakup about six months ago, I replaced a non-attentive boyfriend with an overly attentive job, where 12-hour days are the minimum and you leave your cell phone on 24/7 for emergency work calls. Tonight, however, my boss vowed not to call, so Kate knew the last thing I wanted to do was go home.

The next three hours go by like five minutes. Mr. Hawaii is from the Midwest like I am (Milwaukee and Chicago, respectively) and even used to attend the same church I go to. We talk about the Cubs versus Brewers, if we’re more dog people or cat people (dog), and trade stories of our most embarrassing adulthood moments (his was laughing so hard at work once, he wet his pants; mine was giving a toast at a wedding about how the bride and groom met—only, the bride had told everyone a different how-they-met story—oops). Suddnely, it’s 2am. Closing time.

We exit and we’re a block from Venice Beach, the infamous boardwalk full of eclectic characters peddling jewelry they made from soda cans and medical marijuana cards, cannabis filling the smoggy air like perfume. “Want to take a walk?” Mr. Hawaii says.

It was a balmy night, almost like we were in Hawaii, especially the way the palm trees swayed under the lights along the beach sidewalk that were so tall they disappeared into the sky. It almost looked like they were producing stars for our impromptu romantic walk.

We walked and talked until dawn. At one point, Mr. Hawaii asked to hold my hand, but nothing else. When the sun started to rise, we sat in silence in the cool sand and watched the sky turn candy-colored orange and pink, swirling together like an ice cream cone. At almost 7am, Mr. Hawaii asked for my phone number, I got his, too, and then said he’d better go let his dog out, a cocker spaniel named Brewer. He was going to walk home a couple miles and I offered him a ride.

I really needed to use the bathroom before my half-hour drive home. Of course, Mr. Hawaii had a bathroom…

After the bathroom, we really were just going to “take a nap”—after all, we’d both pulled an all-nighter. But once we were in such close proximity to each other on his bed, then the shower, then against his bedroom wall, forget it. I think we finally fell asleep around 9am. For the first time in months, I felt truly present with someone, not just physically, but mentally as well.

That afternoon when I left, we agreed that it was “fun,” but both had excuses not to see each other again—I was still mourning my ex, he had given up on women and was “dating his dog” (his words).

We hugged, kissed one final time, and that was that.


I never understood one-night stands. I certainly knew, though, that they didn’t turn into anything past that night. The social mores made the connection a physical one, not an emotional one. But, with Mr. Hawaii, even during the pre-sex part of the evening, we exchanged much more personal information and tidbits about our lives than I did on many of my pre-planned first dates. And our outing had been two or three times as long as a regular meet-and-greet type of date. Aside from the physical aspect, we both seemed to crave the companionship, someone to talk to or walk with, no matter how fleeting, even if the beach conversation turned out to be foreplay. Whatever the one-night stand definition was, I felt ours was different somehow. I liked how it gave me hope that I was desirable to a guy again, that I could go out and meet someone—a stranger at a bar, an online date—that someone wanted me.

The day after I left Mr. Hawaii’s house, I couldn’t find my wallet. It had been in my pocket the previous night, and I remembered seeing it at Mr. Hawaii’s place. Oh, no! I had to call my one-night stand! Shyly, I did. What else could I do, ask a friend to go get it? I called and Mr. Hawaii said he’d be at the dog park soon, if I wanted to meet there.

I was nervous to see him in the daylight—would he remember what I looked like without being in a post-beer fog? Would he be aloof or nice? Was the version of him from the night before the real version or the acting one (which is quite common in L.A.)?

The walk across the dog park seemed miles long, but was probably about 20 feet. We spoke awkwardly for a couple minutes, staring at all the dogs instead of each other, both confessing that we slept the rest of the day away after I left his apartment. Then we played catch with his dog for about 20 minutes. Finally, he said, “Right. Your wallet.” He handed it over. As he did so, I thought everyone in the dog park was staring at us with their, “We know you two hooked up” faces. I thanked him and headed for my car. “Hey,” he called out, walking over to catch up to me. “Want to go grab some dinner?”

That dinner turned into several more, and suddenly Mr. Hawaii and I were dating. Lunches, dinners, dog parks, beach walks, studying, laughing, going to parties, going to diners at 3am for pie just because, meeting each other’s friends. He added a juvenile, free-wheeling aspect to my life. He was fun and made my life even more fun. He kept saying he didn’t want a girlfriend, though he sure acted like a boyfriend and was in constant communication with me.

We were inseparable.

However, over the next few months, the more I got to know him, the less I wanted a long-term relationship with him. For instance, he was more flirtatious than I was comfortable with and wasn’t focused on what he wanted to do with his life (he was between short-term jobs and said neither were the right career path). He also drank a lot. Granted, he could hold his liquor, but did we really have to drink every night? The one saving grace was our physical relationship, both of us getting out of our sexual comfort zones and doing one-night-stand-type things, like sneaking out to our car for a tryst in the middle of a party or having sex in a secluded place outside. Another time, I knew which window of his house he left open and snuck inside, pretending to be a stranger. With him, my sexual guard—and his—were down and we constantly acted like sex-crazed teenagers, building up our sexual self-esteem and confidence.

At the end of the summer, as we walked along the Venice Beach Boardwalk, Mr. Hawaii asked me to be his girlfriend. I said no, listening to my instincts. “I think we’ll be better as friends,” I said. He asked why and I said we were in different places in our lives and wanted different things. I thought I wanted this passionate relationship and acting-like-we’re-still-in-college-though-we’re-almost-a-decade-out, but I didn’t. I wanted more and knew that it was out there if I went looking for it, which Mr. Hawaii had inspired me to do.

Though I don’t go out suggesting that everyone should have a one-night stand or a fling at some point, I do think we learn a lot from them. I know a lot of the sexual confidence-boosters and simple, yet spontaneous, fun outings (like to the pie shop) translated well into my post-Mr. Hawaii relationships. After “dating” Mr. Hawaii, I took an opposite approach when getting physical with guys, aiming to wait 90 days before sleeping with someone and truly getting to know them emotionally and intellectually first. (In fact, I recently wrote about it for Bustle.) But, my one-night-stand-turned-relationship was fun while it lasted. And life is about having fun and learning from our experiences, right?

Over the years, Mr. Hawaii and I have stayed cordial. Ironically, he is settled down and engaged to someone he’s been dating for four years, and I remain unattached, a few long-term heartbreaks under my belt since him. But, just like the Venice Beach Boardwalk peddlers, I’ll keep trying.

Related Links: