My Best Friend And I Switched Boyfriends Twice And Somehow Our Friendship Survived And Thrived


Yes, you read that headline right. Yes, it is as crazy as it sounds. Yes, my best friend and I are as stupid as we seem. But hey, it’s not the first idiotic thing we’ve done that sounded like a good idea at the time. Here’s a little timeline of how it all went down because honestly, that’s the only way even I can keep track.

High School, Freshman Year
Enter best friend. Just a little preface, I was a cheerleader all through middle school and high school and I helped coach the middle school team all four years of high school. My best friend, we’ll call her Carly, is a year younger than I am and was also a cheerleader through middle school and high school. Long story short, we bonded over cheerleading and shit talking. It was a match made in heaven.

Sophomore Year
Enter boys. Carly introduces me to two boys at a football game. We will call them Bob and Dave. I liked Bob and Dave, but they were a year younger than I was, so Sophomore Me wasn’t feeling freshmen. However, Dave took my number and immediately texted me after the game. Little did I know that this was the beginning of a long-term flirtationship/best friendship/relationship that would result in many thrown phones, ice cream tubs, cuss words, and tissues.

Junior Year
Enter happiness. Carly and I remain best friends with various ups and downs, which are pretty much irrelevant to this story. We also remain friends with Bob and Dave. Dave and I have settled into this flirtationship/best friendship kind of deal. We’ve never been the best at keeping things simple. Carly comes to me and confesses that she may have feelings for Bob. I, being the busybody that I am, immediately jump all over this. I talk to Bob and through methods similar to World War II torture techniques, and I finally get him to admit that he’s feeling Carly, too. Fast forward a few months and they’re dating. Thanks to me, nonetheless. Fast forward five more months and they’ve broken up.

Senior Year
Enter trouble. Alright, here is where things get real interesting. Senior year was a shit show to say the least. Come December and my relationship with Dave has now progressed to hooking up and then to “talking.” Dave won’t date me because he said he wasn’t a “commitment” kind of guy. Typical dick move, right? Well, he proposes we chill out on our thing for a while and silly me took that to mean that he was done with me.

He asks someone else to prom. Cool. Cool. That’s fine. Whatever. I have no one else, so I ask Bob because I’m really good friends with the guy. I check with Carly and she says she was fine with it. They had broken up 5 months ago and it was just a friendly thing, anyways; I honestly didn’t see a problem with it. I should have known better, but I have to admit that a little part of me just wanted to get back at Dave. The thing with Bob starts out as friends, but soon progresses to more.

Dave tries to get me back and I turn him down because I really thought things could work out with Bob. Well, Dave decides it’s a good idea to go for my best friend. I tell Carly that I am toooootally fine with it because I’m with her ex and I can’t be selfish. IT FUCKING KILLED ME. I was PISSED. SHE BROKE UP WITH BOB 5 MONTHS AGO AND DIDN’T EVEN SEEM TO CARE WHEN SHE DID. THIS BITCH WATCHED ME THROW MY PHONE ACROSS MY ROOM AND BAWL MY EYES OUT JUST A MONTH AGO OVER DAVE, I thought as she sat there and tells me about the things he’s been texting her. But as the good best friend I was trying so hard to be, I smiled and even encouraged the relationship.

Things. Got. Messy.

We kept things from each other. We shit talked each other to the boys and to other friends who knew the situation. We were the most interesting thing to happen to our high school since we beat our rivals in football the previous year.

Things. Got. Messier.

I made out with Dave. While he was with my best friend. While I was with Bob. Am I proud of this? No. Does either of them know about this? Hell no. But Bob and I had a lot of issues. We were never meant to work. And Dave had become my best friend again. It was nice having him there for me when it felt like everything was falling apart. Bob was probably only with me to get back at Carly and I had basically lost my best friend. Dave had always been my go to. He understood me and accepted me for who I was, not who I wasn’t. Carly didn’t even like him that much. It was all just a shit show.

A few weeks later, Dave and Carly end things. I end things with Bob.

College, Freshman Year
Enter COLLEGE. After what I had been through, it was no surprise that I was ready to leave that town as fast as I could, tail between my legs. My relationship with Carly was still shaky, if not completely broken. My relationship with Dave was complicated and painful. My relationship with Bob was surprisingly my strongest friendship out of the three. The first two months of college, I shut everyone out from home. I didn’t want any reminder of the pain and confusion that I had suffered a few months before that. I had to go home at some point, so my first break, I see Carly. We have a very girly, very tearful, very honest night with each other. I completely broke down and told her how much I miss her and how much she means to me. She reciprocates the feelings. Now, we are closer than ever and more honest with each other than we ever were.

Fast forward a few weeks and she admits to me that she never got over Bob. I completely understand. Since Bob and I were still best friends, I use my matchmaking powers and set the two up again. They have now been happily dating for two months.

Don’t worry, I didn’t forget about Dave. Dave and I pretty much stopped when I went to college. He hooked up with a girl at a party the weekend after I left and I had come to my wits end with him. I was done. I spent the next two months joining a sorority, getting way too drunk on what should have been “school nights”, and having a few random hookups. He reenters not too long before Halloween. We have our own tearful night on FaceTime, where he says he just wants me, apologizes for everything, tells me how much he misses me, and promises he’ll change. I was hesitant at first because I was having fun not worrying about a guy from home and hooking up with whomever I wanted to, but after that, it was hard for me to say no. He’s my weakness. So we’ve also been happily dating for two months.

Also, our dating anniversaries are on the same day. So that’s the story of how my ex/current boyfriend and I now share an anniversary with my best friend/his ex and my other ex.

Moral of the story: don’t share boys with your best friend. But if you do, make sure they’re at least really cute and totally worth it.

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