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Hi Damon,

I’ve asked so many friends and friends of friends about this situation. But I think I should get a man’s perspective on this. I met this man about three months ago and we immediately slept together. We both agreed we weren’t looking for relationships at the time. But these days, I find that I get really anxious when I don’t hear from him. I’ve asked my friends, and some married couples about whether or not I should continue “seeing” him. Some of my friends say it’s time for me to stop sleeping with him, so I can clear my head, and ask him about the trajectory of our relationship. I don’t know if I’m really ready to give up the sex. Some married women I’ve been speaking too keep telling me about all these timelines and I’m wondering what I should do. Should I keep seeing him? Am I setting myself up for failure?

– Friend Wanting More Benefits

 

Dear Friend Wanting More Benefits,

In a perfect world, the friends-with-benefits arrangement — where two adult parties agree to have a consistent relationship that consists of sex and nothing else — would be a perfect solution to both the “inbetween” relationship stage where people between relationships need someone to keep them, um, occupied, and the “I just don’t want to be in something serious right now” stage everyone between 25 and 34 seems to be in right now.

It is not a perfect world, though. Although the friends with benefits arrangement sounds great on paper and works well at the beginning, as 99.99999% of people who’ve entered one will tell you, the longer it lasts, the more awkward they become. As good as the sex can be, someone — and it can be the man or the woman — will eventually catch some sort of feelings, and when someone catches feelings, feelings get hurt.

This seems to be where you are right now. You’re not hurt yet, but if he decided to end things — or if he decided to share how much he likes this new chick he’s dating — you would be. The answer is obvious. Let him know how you feel. If it’s not reciprocated, end the relationship. It might be painful, but pulling off a bandaid hurts much less than putting one on a broken heart.

Sincerely,

Damon Young

Pittsburgh native Damon Young (aka “The Champ”) is the co-founder of the ridiculously popular VerySmartBrothas.com Their first book “Your Degrees Won’t Keep You Warm At Night: The Very Smart Brothas Guide To Dating, Mating and Fighting Crime” is available at Amazon.com.  

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