Searching For Satisfaction

The Downside To Dating A Friend

Posted on: February 16, 2011

Lately I’ve been thinking a lot about my past relationships/ dating situations. One in particular has been on my mind a lot – my failed attempt at dating my friend, the Vegas guy.

What seemed like a great idea at the time imploded into a cesspool of failure, and sucked our 5+ year friendship into the black hole that was left behind. The loss of that friendship is what has been on my mind the most. The Vegas guy was a good friend to me, and I was a good friend to him. We were each others shoulder to cry on, sounding board, listening ear, source of inspiration & cakebuddy. I miss that friendship; specifically a friendship with someone who was an “outcast” like myself. We thought the same, tending to be on the fringes of what’s considered acceptable behavior for Black America. We commiserated over shared/similar experiences, growing closer in our support for each other & the parallel life paths we were traveling down.

I miss my friend. I wish I hadn’t even tried to take the plunge at a relationship, instead keeping my attraction at the flirting level. Had I done so, I’d still have my friend & the friendship. Hindsight is always 20/20 and in this instance I feel a bit of regret. It’s not often that I regret things – I tend to live my life with the mindset that every experience is a learning opportunity, and that situations generally work out the way they are meant to. But this situation continues to plague me, haunting me & my thoughts. Losing the friendship that I had leaves me regretting taking the dating plunge at all.

Could I have simply gone back to the friendship, once it was apparent that romance was not in the cards for us? Yes, but it wouldn’t have been the same friendship as before. Our relationship exploration experience opened my eyes to some things I didn’t know about him, and they effected me to the point where I questioned if I could even maintain a friendship with him. I chose to call timeout & not maintain the friendship. It seemed like the right thing to do at the time, and I’m sure it still is. But my heart mourns for my friend & a friendship that I valued.

It’s funny – the past two years of my dating life have shown me that a friendship is an integral foundation for a successful relationship. Yet even the strongest of friendships do not always translate to a successful & sustainable romantic relationship. What works in a friendship could be disastrous when two people transition to significant others. Experience has taught me this lesson.


I miss my friend.

Have you dated a friend? Were you able to go back to the friendship or did you lose that too? Can you go back to being friends after you’ve dated?


4 Responses to "The Downside To Dating A Friend"

I’ve never dated a close friend. I have or rather had a close friend that wanted to date but a) I refused to cross that line with him and b)didn’t have those romantical feelings for him. We don’t talk much anymore; I guess it was just too awkward for him to be my friend after I gave him his heart back with a friendship tag on it. As far as being friendds with an ex, I have a “quasi” friendship with an ex. Its taken a long time for us to get there. Its still a little weird but he feels comfortable enough to ask me for girl advice. So I guess that’s progress.

Awwwwwww…. Don’t be so hard on yourself. If you miss the friendship that much, then try to work on it. But I agree, it’s hard to be friends with someone you were in love with. I can’t do it.

there’s no way to know if a great friendship would translate into a great relationship unless you try. i was friends with most of my exes before we got together. do i regret dating any of them? nope.

I’ve dated a friend or two. I even dated one of my BEST friends. And guess what? We remain friends to this day and we’re both happily married to someone else. We didn’t really speak for about 6 months after we dated, but then we just reconnected and never stepped over the line again. It just wasn’t a possibility. Been there, didn’t want that. Moved on. We have been platonic friends for about 11 years now.

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