This Is What Happens When You Hire A Gigolo And You Have An Almost Boyfriend

We've all been in that awkward stage of a relationship where you're still hiring gigolos, but your heart just isn't in it, am I right?
Publish date:
March 11, 2013
gigolos, almost boyfriends, cowboys4angels

You guys are the best. The Internet, that is. You helped me pick the sexiest, hottest gigolo that my little brain could ever dream of -- Trent from Cowboys4Angels -- having escort me around New York City in the name of crass journalistic stunts.

You even helped me pick out the fantasy: Him giving me compliments the entire time, or "ego cunnilingus" as I like to call it.

And then I got an A.B.

An Almost Boyfriend.

Over the course of three, four, five dates with the Comedian who I've been seeing, I found my heart just wasn't into the prurience of the whole endeavor anymore. Goddamn you, A.B. Goddamn you.

Probably the clearest signal that nothing was going to happen between me and the Gigolo right off the bat? One of the first things I did was show him a picture of the guy I'm dating and then after that, some video of him doing a stand-up set. Which men love, I've heard. To be compared to other men. Especially right off the bat.

To the Gigolo's credit, earlier in the day, I had received flowers from his boss, Garren James, who runs Cowboys4Angels, with a slew of compliments on the card, including "Youa Re A Great Success." I imagine Garren and Trent were so overwhelmed with emotion for me, that the spelling got jumbled.

Quite charmingly, the Gigolo didn't restrict the slew of compliments to only me either. When he arrived at xoJane headquarters, three women immediately rushed into the Clubhouse where Emily, Corynne and I work to say, "YOU HAVE A REALLY HOT GUY WAITING FOR YOU!" One woman added giddily, "AND HE JUST COMPLIMENTED ME ON MY HAT!" I didn't want to break her heart that this was part of the male escort arrangement I had paid for, but you know, I did anyway.

"But I'm sure he also really did like your hat," I added, smiling and patting her arm. "I'm sure he did."

When the Gigolo met Emily and Annie, he looked at the group of us and remarked, "Wow, everyone here has such pretty eyes. Is that a requirement for working here?"

Nice, Gigolo. Nice.

Olivia was busy in Jane's office helping to prepare for our boss's epic SXSW presentation, but before the Gigolo arrived, she confided in me that she would actually be interested in dating him. The real highlight of our "date"? Doing Facetime with Olivia later that night while the Gigolo was still over, and him saying he definitely wanted to take her out.

I cannot wait to be the maid of honor at that wedding. "Funny story how they met." (That joke is courtesy of the Comedian, by the way.)

After giving him a tour of xoJane, the first thing that I did with my Gigolo when he arrived at xoJane was ask him to take his shirt off -- solely for the sake of great visuals, obviously. Although I did feel a little bit like a strip club owner chomping on a cigar asking the girls to dance for me.

But it was worth it: Because I got to write our Web site logo on his pecs in pink lipstick. Then I kept having to rub it off and start again to get the logo just right, but somehow I powered through. Annie supervised.

After these lipstick-on-the-abs pleasantries were out of the way, we grabbed a cab back to my place where the first thing the Gigolo did was teach my dog Sam a new trick: how to "lie down."

When I told the Comedian that he taught my dog this, he said: "Of course that's the first trick he taught him." Oh, and you may be wondering at this point, why the Comedian is my Almost Boyfriend and not just my Boyfriend. Well, because we had That Talk, and he said, "Listen, just for the week that you do the gigolo story, I don't want to be, like, 'the boyfriend who's cool with you hiring a gigolo -- and oh, what does he think?' I'd rather just be dating for that week. It's not that I don't want to be your boyfriend, but I think you understand where I'm coming from. Like what am I supposed to say, 'Hey! Yeah, it's totally great. I mean, sometimes I hire the gigolos for her. It's awesome.'"

Fair point.

Or as my friend Michael notes: "Wow. That's a strong move on his part. Nicely played."

I told the Gigolo all this, too. Of course. And he, in turn, told me stories from his life and "work." These included generalized (so as to not reveal client confidentiality) stories of his companionship during his time working for Cowboys4Angels (about a year) that ranged from the tender (a woman who had lost her husband and wanted someone to spend Valentine's Day with) to the uber-no-fucking-around career woman (who flew him to Vegas and booked him a hotel room because she didn't have time to date).

I must tell you that I've decided not to post a picture of the Gigolo's face here because I had an odd experience after my time with him. After interviewing the shit out of him (as is my style), I found out that he goes to church every Sunday, became a gigolo after he found out the long-term girlfriend he was in love with was cheating on him and is doing this to support his mom who has taken ill.

No. Lie.

And how many people actually know that he is doing this gigolo racket? Well, that would be no one.

"Do you have a therapist?" I asked. "Can you talk to any of your friends?"

"No," he said, and then, remembering his compliment duties to me: "You have a really beautiful smile, by the way."

"Thank you," I said. "So wait, does your roommate know?"

"Nope," he said, and I shook my head in disbelief. Like, I have trouble keeping a secret from the Starbucks barista, let alone every single fucking person in my life.

"You have beautiful hair by the way," he added, ever playing his part in my compliment fantasy. "It's really beautiful."

Funny, I never realized I could get sick of compliments. Maybe it was getting them "professionally" that took some of the shine off.

Honestly, though, the more my Gigolo talked, the more I really hoped that he would end up with Olivia. He doesn't tell any of the women that he dates that he does escorting, and I want this dude to believe in love again. He certainly believes in compliments. Don't believe me? Over the night he told me:

"You have an awesome laugh." "You have incredible, long legs." "It's very cute when you bite your lip." "I like the way you say, 'Totally.'" "You have a great body, and you show it off well." "You have very sexy eyes the way you look at people. It's very mysterious and devilish." "I like the way you take charge. You're very demanding." "I like how you talk about the guy you're dating. I can tell you really like him." "At the office, it seems like you're the life of the party, and the room is full of laughter when you're around." "You're very smart." "I like how well you type. I think you type about 100 words a minute."

That's right, baby. MY TYPING.

At that point, I knew that my erotic night was coming to an end. Although I guess I could have done a little copy editing to really get him going.

As he headed toward my door, I figured it was time for me to return the compliment love.

"You're a great gigolo," I said, as I gave him a hug, "and I think you'll make a great husband for Olivia."

He laughed. "Oh, yeah," he said, "you're also very funny."


So my Almost Boyfriend tells me.


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