I Sent My Best Friend Undercover To My Ex's Bachelor Party

I asked my friend to go as a French maid singing telegram to my ex's bachelor party.

group of male friends at bachelor party bbernard / Shutterstock

During the nine months that Jerod and I dated, I'd cheated on him for over half of it with his eccentric friend Stefan.

When I was forced to choose between the two of them, I chose Stefan.

I told myself I didn't want Jerod, but that didn't mean I was completely over him or that I didn't want him to want me. 

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I was still obsessed with him.


No, it doesn't make much sense, but when you're in your early twenties, pretty enough for choices but still insecure, your actions can defy logic.

I'm not sure Jerod and I were friends when he and his rebound girlfriend decided to get married.

Our relationship would go through many incarnations, and it isn't easy to pinpoint what our status was at the time.

Whatever it was, I wasn't invited to the wedding, because of course I wasn't. Why would I be? 

I knew there were still unresolved feelings between us. I'd seen how he looked at me at our friend Robert's wedding.

'd been wearing a pink tee-shirt dress that was probably just a long tee-shirt and not a dress at all as it was extremely short. I told myself I could get away with it. Jerod and my eyes had locked, and I felt that chemistry we always had. I reminded myself that Stefan and I were together now, and Jerod was with Sara.


I tried not to be jealous of Sara as she was younger, a dancer, and much less cynical than I was.

Besides, Jerod was determined to marry Sara and I had no right to want to stop him.

And at the time, my life wasn't where I wanted it to be.

I was working as a long-distance operator and would often get the 10:00 pm to 6:00 am shift, putting through calls to Manilla, Philippines, and Oaxaca, Mexico. While I waited on the line for the call to go through I'd dream about moving to L.A. and pursuing a comedy career. Sometimes I imagined my life if Jerod and I hadn't broken up.

When my shift was over, I'd wait at the bus stop writing bad poetry in my mind about how much better my life was without Jerod in it. I did this partially to stay awake and partially to remind myself I was over him.


I wasn't writing poetry — not in my head or anywhere, about Stefan.

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I didn't want to marry Jerod, but I didn't want anyone else to marry him, either.

The wedding was happening and there was nothing I could passively aggressively do to stop it.

Although I was a drama major, I had enough sense to know that was a bad idea to crash the nuptials. There was no logical reason for me to be there as the ex. I didn't do flowers or work as a cater-waiter and besides, Jerod and Sara were keeping it small with just close friends and family.

Stefan and I were still together but I'd effectively ruined his and Jerod's friendship, so he wasn't considered a friend.


Besides, how could I ask my current boyfriend to stalk my former boyfriend and his former friend?

My brilliant and beautiful friend, Caitlin was working for a singing-telegram company at the time to earn a little cash while she figured out what she wanted to do with her life. For her job, she dressed as a sexy French maid and sang songs to whoever was the recipient of the telegram.

I don't remember if Caitlin volunteered or if I coerced her, but she agreed to crash Jerod's bachelor party as the entertainment. 

It seemed like a brilliant idea at the time.

I'd done a little detective work and found out the location of the party which was our mutual friend David's house.


Caitlin got dressed up in her super-short French maid dress with the multiple petticoats, her perky cap, and her stockings, grabbed her boom box, and off she went to Jerod's bachelor party.

I don't know what I wanted her to discover.

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Was it that Jerod still loved me or that he was as obsessed with me as I was with him?

I anxiously awaited to hear what she had to report when her undercover mission was over.

By the time she got there, the party was underway, and Jerod was halfway to oblivion. There was a party area set up in the backyard that was tented, with pillows, and cushions, but the main house and porch were also available for party-goers.


Jerod knew Caitlin from our time together, and his eyes grew wide when he saw her on David's porch. Her disguise as a French maid fooled nobody.  

David wouldn't let her go back to the tented party area.

I found out later that's where the stripper was, but instead of enjoying the show out back, Jerod chose to stay and see Caitlin's performance. He knew that if he did anything inappropriate or too handsy, it would not only be awkward but that she'd report it back to me.


Neither Caitlin nor I can remember the song she sang, but I like thinking it was Tina Turner's, Private Dancer. I picture her in her little outfit, singing the lyrics, "I'm your private dancer, a dancer for money," while being flirty with her flouncy skirt." 

Caitlin finished her song, and everybody applauded and tipped her for her spectacular performance — she was a talented singer. Then Jerod sat on the porch with her, eating cereal and talking. Instead of a night of rowdiness and debauchery, Jerod had a restrained, low-key stag party. 

If I'd wanted Jerod's party to be a bit of a bummer, mission accomplished.

Afterward, Caitlin had nothing to report — there'd been no bad behavior or declarations of love for me. He was happy and excited to marry his soulmate, Sara.


I needed to move on because obviously, he had. 

The wedding went off without incident and when the officiant asked if anyone objected to the union, no one said a word.

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Christine Schoenwald is a writer and performer. She's had articles in The Los Angeles Times, Salon, Bustle, Medium, and Woman's Day.