The Big Ask

In 2013, I had a major crush on one of my friends. I hesitate to say I was in love with him, but I really cared about him. A whole bunches a lot. I might have loved him had he returned my feelings, but he only saw me as a friend. It’s not a particularly novel tale. You’ve probably heard it before. Certainly nothing to write home and tell the wife and kids about, assuming you have a wife and kids. If so, lucky you.

For a while, he and I had been friends with *limited* benefits. He thought I was cute, and he admired my physique, and we made each other laugh, but he didn’t buy into the myths of dating and monogamy. So we’d kiss and make out and spend the night at each other’s apartments, and although we got physical, we never went all the way. He said he was scared to have sex with me, because unlike the random guys (plural) he did have sex with—the evidence of which I often found in the form of discarded condoms in his bathroom trash can—I meant something to him. Lucky me.

This wasn’t a problem until I really got to know him. On the surface, he was pretty much the definition of everything I didn’t want in a guy. He was somewhat of a loose cannon, messy and unpredictable. Also, whereas I preferred the clearance rack at Express Men, he willingly shopped at thrift stores, scouring them for treasures like some kind of godless heathen. And yet, underneath all that swirling chaos, he was one of the sweetest guys you could ever meet. I asked him to consider dating me and made it clear that I wasn’t trying to force anything. If something happened between us, great. If not, no biggie. He said he’d think about it. Fair enough.

The last week of May, he called to tell me that he would be going out of town for a month (the day before he would be going out of town for a month). The morning before he left, while helping him run some errands, I asked him if he thought we’d ever be more than what we were, and he responded, quite honestly, that he didn’t think we’d ever be in a committed relationship. Later, he further revealed that even though he found me attractive (naturally), he didn’t know what to do with me sexually.

Just to break this down for you: After a decade of working out specifically to get in shape so that guys would find me attractive, the guy I liked a whole bunches a lot was telling me that even though I was in the best shape of my life, he did not want to have sex with me despite his ability to appreciate how handsome and fit I was.

Game over. Thanks for playing. Please enjoy this parting gift of WTF!?! YOU’VE GOT TO BE KIDDING ME!

I tried not to let him see, but I was devastated. After I left his apartment, I drove home, and I sobbed intermittently throughout the rest of the day into the evening. We had never even officially dated, yet somehow, he’d managed to break my heart.

While he was out of town, I thought about him constantly, even when I didn’t want to think about him. I tried finding someone else, but although I downloaded Grindr, Jackd, Hornet, Tinder, and OKCupid on my iPhone the night he left town, the few tribunes who stepped forward to volunteer and replace him weren’t seriously viable options. Eventually, I stopped trying to fight it, because thinking about him made me happy, and I still had hope that he might somehow fall for me once he returned.

Our mutual friends told me that I should get over him as if I were magical and possessed total mastery over the human heart. They also told me, erroneously, that I could do better. The only bad thing about him was that he didn’t believe in monogamy, and I didn’t need him to be monogamous. I knew exactly who he was when I fell for him. If he wanted to play the field, fine. I just wanted to be home base—for at least a season.

He ended up being away for more than one month. The first month he was away, he came back to visit for a few days, and I saw him once, but something was different. He let me spend the night at his place, which was incredibly nice of him considering I could easily tell that he didn’t want me there. I knew then that I’d have to get over him, and in the month that followed, I tried my best to do so.

When he finally returned to town in August, I asked him out to lunch as a friend. While sitting at a busy pizza joint in Pasadena, I asked him how he’d been the past month, and he told me that he’d had a boyfriend for two and a half weeks while he was away. I figured that he would be having sex with guys while he was out of town, but a boyfriend? While I’d pined the last two months, writing Carpenter-esque love songs and thinking about him daily, he’d gone out and formed an emotional attachment with someone he’d met on Grindr. It was my worst nightmare. Even though he always said he didn’t want a boyfriend, I knew he would eventually meet and fall for some guy and change his Facebook status to “in a relationship” if only to crush whatever was left of my spirit. Yes, I had anticipated it. But not so soon.

Following this revelation, the most humane course of action would’ve been to carry me out back and shoot me between the eyes, Old Yeller style. Instead, he continued on, describing the guy as having a soccer build.

“A soccer build,” I asked? “Isn’t that, like, my build?”

“Yeah”, he agreed.

So, not only did he date this guy, but the guy had a similar build to my own, and somehow by the grace of God, he figured out what to do with him sexually every day for two and half weeks. But with me, it was all shrugs and thumb twiddles.

Originally, I had asked him to lunch, because I had a favor to ask. A big one. This new information was going to make it awkward, but I had to ask anyway.

You see, I was about to turn 30, and I’d never had a boyfriend which was all I’d ever wanted since my first crush on a boy at the age of 14. One night, when I was 21, I sat in my apartment, bawling my eyes out and praying that some wonderful fella would come along before I was 30, because nine more years seemed like an awfully long time to be alone.

And they were. Long and awful indeed.

Nine years later, when August 3rd rolled around, a month before my birthday, I had to accept the fact that I wouldn’t have a boyfriend before I turned 30. In the same way that if you don’t have a Valentine’s date two weeks before Valentine’s Day, you can give up the hope of having a Valentine, I knew that it was too late. Then, one day, the thought occurred to me to ask him if he would be my boyfriend for a week. It wouldn’t be exactly what I’d wanted, but it’d be something, you know? Besides, I had no other options. He was the only person I could ask, because not only was he someone I cared about, but we had also been friends with *limited* benefits before he’d left town, so it’s not like we hadn’t been physical before. I was just asking him to do what we had been doing, but instead of once every two to three weeks, seven days in a row.

Still, I knew this was a lot to ask of him, and I figured he would probably say no. But I was afraid to ask which meant I had to ask. Because whenever I was afraid to do something, it usually meant that it was important to me and worth the discomfort.

So I asked him to be my boyfriend for a week, and I explained my reasons why—how I wanted to have a boyfriend by the time I was 30 but had not (which he already knew), how I didn’t want to start my 30s filled with anger and sadness, and how if he said yes, it might break the seal and get the ball rolling on the whole “me having an actual boyfriend” thing.

He listened intently to what I had to say, and he agreed not only that it made sense, but that in a way, it was pretty genius. Regardless, he said no. And he had every right to do so. I didn’t want him to say yes if he didn’t want to do it. I just hoped that, somehow, he would.

Out of curiosity, I asked him why, and he explained that he wouldn’t feel comfortable, because he felt I would expect certain things from him like kissing and spending the night with each other. We had been doing these things as friends before he left, but now he didn’t want to be physically intimate with me.

Once again, just to break this down for you: He was cool with kissing strange guys and spending the night with them and even having casual sex with them, but when doing those things would mean something—like really mean something—to someone he knew and cared about, he couldn’t do it.

And so, he said no. Because for a week, he would have felt awkward. I’d been drowning in a tremendous, black abyss of loneliness and disappointment for 15 years. God forbid that he should feel awkward for a week. Could there be anything worse?

We finished our lunch, and he was sweet and tried to be helpful, offering advice about how I should focus my energy on something else (as if I hadn’t tried that at least a thousand times in the past 15 years). And then we parted ways with a friendly hug. Later that day, he messaged me that he was sorry I was hurting. But I doubt he thought about it much after that. Not because he was heartless, but simply because it wasn’t his problem. In fact, when he was out of town, a fortune teller told him that he was going to marry a doctor and be famous at the age of 27. For him, it was all good times and rock n’ roll ahead.

The thing is, I wasn’t mad at him. I couldn’t be. He didn’t do anything wrong. He was always honest with me, and I even understood how he could fall for someone else and not fall for me. Still, it hurt.

It hurt that I’d never had a boyfriend. It hurt that while I was thinking about him every day for two months, not only was he not thinking about me, but he fell for someone else. It hurt that I had to ask him to be my boyfriend for a week. And it hurt that I would have done anything for him, but he couldn’t find it in his heart to do something that would’ve made a meaningful difference in my life. Once again, wasn’t mad about it, totally got it, but it didn’t make it hurt any less.

As humbling as it was to ask him to be my boyfriend for a week, I’m glad that I went through with it. In a way, I think I had to in order to let him go. Which I did.

Years later, on his 28th birthday, I noted that the fortune teller’s prediction had not come true as he was neither married to a doctor nor famous. Which must have been a disappointment for him, I’m sure. Perhaps even similar to the disappointment I felt when I never got a boyfriend before I turned 30.

But what could we do? Some things just weren’t meant to be.

* * *

Note from the Writer

If you enjoyed this personal essay, you might also this original short story:

Or my essay series about my year in quarantine:

Also, hearts and tips (though never mandatory) are especially helpful and greatly appreciated.

Thank you for reading.

Navaris