Real Friends Let Friends Learn from Their Dating Mistakes

I remember we used the alias “Bert” to talk about my best friend’s 6th grade boyfriend “Ben.” We felt like secret agents. She can recount—from my shirt down to my shoes—what I was wearing on the day of my first kiss. She knows because the outfit was hers.

We have known each other for more than half of our lives, which means we have witnessed every awkward haircut and change in screen name, and all the different breaks: the skin breakout, the family breakdown, the bitter breakup, the agonizing heartbreak. She was there to get me tissues when I teared up in class after a run-in with my ex-boyfriend in the hallway. I came to her house with pint of Chunky Monkey after she found out her crush was moving to Missouri.

This winter break, we came together in my parents’ kitchen and laughed over how painful those minor heartbreaks felt at the time, and how silly they seem in retrospect. My ex-boyfriend is still wandering the high school hallways, working on graduating, and her crush in Missouri now plays for the other team.

Acting on a playful indulgence, or maybe something deeper, we recalled and wrote down, one by one, each of our boyfriends and sort-of-boyfriends and barely-boyfriends. There was the impulsive artist who said “I love you” and took it back the next day, the emaciated poet who found someone new in less time than it takes for milk to curdle, the detached engineer who introduced me as his “friend,” the gargantuan football player who had a thing for feet. We relied on each other to fill in lacunae of our romantic memory—the men we tried to forget, the boys we had actually forgotten. The historic exercise took us all the way back to our middle school mini-romances, where things got blurry, and our hair was a lot frizzier.

The last boy on my list was Sam, whom I had a crush on in the 3rd grade because of his budding chivalry: he agreed to trade his pizza school lunch for my lifeless PB&J. The next day, he asked for his pizza back, and I cried and told him I had already eaten it.

We looked over our lists, comparing notes. She reminded me to add the Indian guy who told me kissing his ex-girlfriend was like “kissing my mother.” She crossed out the boy in 8th grade who would only talk to her on his GuitarBoy555 screen name, because neither of us could remember his real name.

Needless to say, we noticed some alarming similarities. There were so many a**holes, sleazebags, and dunces. And worse, there were so many blinding red lights, where we should have run—so fast and so far that we never looked back. But we didn’t. We stayed, again and again. How could we have been so stupid as to stay? Or more importantly, how could we have let each other?

I admitted to her then that I always thought her last boyfriend was an idiot, and she told me she always thought mine was a loser. But we loved each other too much to say anything. So we said things like, “I’m happy if you are!” It’s the romantic equivalent of trying on a dress and your friend telling you, “I don’t think I could pull that off, but you totally could!”

I know Shakespeare says love is blind, but he never said anything about our best friends. What about their eyes? They can still see. If we had only been upfront with each other, there would have been no pain, no mistakes, no “WTF” relationships that in retrospect feel like a drunken dream, years lost and Friday nights ruined.

But that’s when we realized; we would never get back that time, and we didn’t want to, either. We needed to learn for ourselves, sometimes more than once. We need to make our own mistakes. “Duh” from a best friend won’t cut it, because the things we wished we had known, we somehow manage to forget again. My best friend knows me better than anyone else, but she doesn’t know me better than I know myself. In the end, it’s my heart, not hers, that’s on the line. I will always value her opinion, but I could never break up with a guy just because she told me to. She would never tell me, either, because it’s up for me to decide.

When we are in bad relationships, we think that we see things no one else can, that no one understands a relationship except the two people in it, that we are the ultimate exception. I remember when a boyfriend from high school and I decided to stay together our freshman year of college, even though our schools were five hours apart. A friend of his mother’s told us, as he poured congratulatory wine into our glasses, “just give it til’ Thanksgiving.” We were outraged. We were different. We could do it. And, in fact, we did make it past Thanksgiving, but not by much. But still, we needed to try it first.

That is where our true friends come in – not to tell us “I told you so” when we lose the race, or make us give up completely – but to be there at the side line, no matter what, with water (or a tub of ice-cream) in hand.

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