I Paid $800 To Take An Escort To A Wedding & He Was Worth Every Penny

Hooking up at my friends’ weddings is one of my favorite pastimes. Unfortunately, when it comes to family weddings, random hookups are generally frowned upon. I was approaching my third one this year and couldn’t bear the judgmental comments about my single life, so I hired an escort. It was the best money I’ve ever spent.

  1. My family is judgmental AF. It’s not a rare occasion for me to be approached by an aunt or conservative cousin with a variation of these words: “Why aren’t you in a relationship? When I was your age, I already had my first child. The clock is ticking!” I’m happy with my single life so it didn’t really bother me at first, but the incessant reminder that I’m some sort of failure for not procreating or landing a husband drove me nuts after a while.
  2. I got the invitation to my thousandth cousin’s wedding and I was over it. I have a huge family, so I go to at least one wedding a month in the fall and spring. It’s insane, I know. I knew the moment that I pulled the mail from my mailbox that there was another wedding to add to my calendar. It’s like the opposite feeling you get from those college acceptance letters in high school. In lieu of joy and excitement, I feel a wave of nausea and dread.
  3. I suddenly felt desperate for a boyfriend. As I looked at the invitation, the words “and guest” stared back at me in an extremely judgmental way. I’m focused on my career and love my single life, so why does this thick piece of paper make me feel so insecure? It took every ounce of my energy to control myself from ripping the invitation into 300 pieces. Instead, I accepted the invitation for myself and my guest.
  4. I scrolled through Tinder for hours before finally realizing what I needed to do. As if Tinder was really going to provide me with anything more than a one-night stand, I scrolled through a slew of men for someone that looked like they were serious. No luck. I’m pretty sure I’d seen a movie where a girl hired an escort for a date—would that be a totally insane idea? Obviously, I know nothing of the escort industry (is it even legal?), so I did a quick Google search. I didn’t want to accidentally hire a male prostitute, so research was key here.
  5. I found a pretty legit website. The very first result to pop up on my search was a website called Rent A Gent. The website was recommended by Buzzfeed and some other reputable sites, so I was confident that this was in no way illegal. Prices were steep, about $200 an hour, but if I was really going to do this, I wasn’t going to hire some Craigslist actor.
  6. Picking a “gent” was like shopping for a boyfriend. I wanted tall, dark and handsome. I stand at 5’8” and always feel insecure in heels with a man since I tower over them. I went with Lee, a super sexy guy with chiseled features and a hint of rugged manliness. I hired him for four hours. Don’t do the math—it’ll make your jaw drop. I felt nervous and excited all at once. The thought of fooling my judgmental Aunts made me giggle throughout the day. Suddenly, I felt something that I’d never felt before a family member’s wedding: anticipation.
  7. It was the day of the show–I mean wedding. The night before the wedding, I was so anxious that I only slept for about an hour. I know this because my Fitbit tracks my sleep habits. He met me a little before the wedding in my hotel room so that we could get acquainted. He was so hot, you guys. I gave him the lowdown on my conservative family and he asked me why a beautiful, intelligent woman like me needed to hire an escort. I liked him already.
  8. I could feel everyone’s eyes on me. I’m not sure who was getting more attention, the bride and groom or me and my date. Family members pulled me aside to pass on their approvals and every woman who shook his hand blushed feverishly. He called me “babe” and held my hand. He twirled me on the dance floor and jumped into the photo booth with me. It felt nice to have a “boyfriend.”
  9. Four hours and $800 later, it was over. Like Cinderella at midnight, it was time for me to lose my perfect boyfriend. Part of me felt like I caught some feelings for him. He was charming, handsome and chivalrous… but he was also acting. It was clear that I was more smitten with the idea of him than the actual gent. Not only did he take the heat off of my single life in a normally awkward situation, but he inspired me to find more of a life balance in a career-focused time of my life. He was worth every dime.
Caitlyn is a freelance writer living in Washington D.C.