What ‘Gilmore Girls’ Got Wrong About Sleeping with Someone Who’s Engaged


But, as you likely suspected, affairs often don’t look like they do on the show, where your lover flies you to his luxe apartment in London and takes you to eat at a Michelin-starred restaurant afterward. Just take it from these four women who’ve been there, done that and shared the details of their affairs with us. 

“I did it for the thrill.”

“I spent three months sleeping with an engaged man. Just like Rory, he’d have me over when his fiancé was out of town, which was a lot because she traveled for work. I met him one night when I was out at a bar. We hit it off, and he told me he was engaged—but not really into it. He actually said that about his fiancé! Unlike Rory, I knew getting involved with him wouldn’t lead to anything serious, but I did it for the thrill. It was an adventure hooking up with an almost married man. It eventually came to an end when he started to think she was catching on and got suspicious. I believe they’re married, and I think she’s pregnant. I wish them all the luck and love in the world.” —Jess M., 37

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“I didn’t know he was engaged.”

“About five years ago, I met a guy at a bar. He was super shy and had this rocker vibe. I was instantly attracted and liked the challenge of getting him to open up to me. We flirted over lots of beers, and one thing led to another. We went back to his friend’s place and spent the whole night hooking up. We even cuddled on the couch until the morning. It was a lot of fun. After it happened, I figured we’d still get together. He even texted me the next day to plan a date that week. I somehow found him on Facebook and saw that his relationship status was ‘engaged.’ I was sick to my stomach. I had no idea. His friends saw us kiss and didn’t say anything. I texted him, calling him out, and he said that she lives in Florida and it doesn’t have to be a big deal. The whole thing was messed up. We never spoke again. I don’t know if they got married, and I honestly don’t care. I still feel disgusting about the whole thing.” —Jenna B., 28

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“We ended up together.”

“This wasn’t the way I wanted to meet my husband, but we got together when we were both engaged to other people. We met at work and started just casually grabbing lunch. Eventually, we both admitted that we had feelings for each other. The problem was that he had been engaged for about six months, and I had just said yes to marrying my boyfriend of two years. We were at an age when we wanted to settle down, so we both rushed into relationships with people. We both say that meeting each other was the right thing to happen at a very wrong time. After sleeping together for a while, we both called off our engagements and became official a month later. We have been married for three years. Sometimes you meet the right person when you’re about to marry the wrong one.” —Leslie G., 35

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“I slept with him for closure.”

“Of course I laughed out loud when I watched Gilmore Girls this weekend and saw the scene when Rory sleeps with Logan—because I was in that situation, too. I broke up with my boyfriend of three years because I felt tied down and overwhelmed. A year laterb I was still single, and he was in a relationship with someone else. He even proposed to her! It was way too quick. When I found out through a mutual friend that he had asked her to marry him, I called him up and asked for a closure coffee meet-up. He came, and we ended up hooking up. In a weird way, I was able to get over him after that. He ended up marrying the other girl. I think I just needed proof that he’d give in to me once more before letting him go.” —Connie H., 29