Caught In the ‘Messy’ Middle: My Best Friend Is Marrying My Other Best Friend’s Ex-Girlfriend. Should I Attend the Wedding or Lose a Longtime Friend?

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I’m caught in a messy situation between two of my best college buddies, Leon and Dupree, and a woman named Robin.

My buddies Leon and Dupree, Robin and I all attended the same high school. Dupree and I attended on football scholarships and Leon on an academic scholarship. We would go on to become roommates and the best of friends throughout our college years. We’ve had some dope times together.

Wedding blues
Laughing group of friends in discussion before pickup basketball game on outdoor court at sunrise (Stock Photo – Getty)

Leon has been dating his high-school sweetheart, Robin, for several years now. Upon graduating high school and entering our first year in college, which was Robin’s last year in high school, Leon cheated on Robin. In Leon’s defense, living on a college campus in coed dorms just proved to be too tempting for him, and he fell victim to the temptation. I know — it’s a weak excuse, but hey. However, by the end of the summer before Robin’s freshman year in college began, Leon had finally worn her down, and they were able to reconcile after the mishap.

After graduating college, Leon and Robin agreed that Leon would move out of state to establish things for the two of them to start their lives together. Leon followed a job to Charlotte as a marketing manager, which kept him very busy. During the time that Leon was away laying the foundation for him and Robin, Dupree swooped in and made a move.

The moon, sun, and stars must have aligned in that man’s favor because he scored in the figurative and literal sense. Robin was more than receptive to his advances, and they became an item after she hurriedly broke things off with Leon under the pretense that she wanted to remain in the state near family. Divergent paths, as my homeboy would say.

I’ve never seen Leon cry. This man cried on my shoulder, and I’m talking about a full-blown all-out, shoulder-shuddering cry. He was heartbroken over Robin breaking up with him, and the saddest part was that he didn’t even know that Dupree and Robin were a couple. He had seen them on Instagram together but didn’t think it was anything serious. Our crew didn’t have the heart to tell him, and he just hadn’t found out up until now.

Dupree and I play on the same flag football team, so I see Robin at practices and games. We’ve become super tight, Dupree and I, since Leon departed. He admitted to me that he had always had his eye on Robin and that when Leon moved away, he was determined to have her. He ended up seeing her at a pool party in the complex in which they lived. One thing led to the next. They ended up hooking up, and he officially made her Bae.

My dilemma is this: Leon is in town to attend a concert, and I’m picking him up from the airport. He’s not nearly over Robin and still talks about her regularly to an unhealthy degree. As soon as Leon landed, I received an Instagram notification from Dupree. He and Robin were Instagram official, using the platform to announce their engagement.

By the time Leon reached my car, the damage had been done. He saw the same post because he made a habit of lurking on Robin’s page regularly. He faulted me for not telling him and was pissed that he had to find out through Instagram. I feel terrible, but it wasn’t my place to blow up Dupree and Robin’s spot in my opinion.

As far as remaining close friends with Dupree, I didn’t feel like I should have to choose a side. I’m a grown man who prides himself on not being messy and petty, but Leon says our friendship is over if I go to the wedding. I value my relationship with both of dudes. Dupree and I have grown closer since Leon moved away, and we’ve been playing in our league. He and Robin seem good with and for each other too.

Am I being a bad friend for not having told Leon that Dupree and Robin are a couple? Should I go to the wedding and lose Leon as a friend altogether or forego the wedding and remain true to Leon?

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NOTE: This story has been edited for clarity and grammar.

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