Q: Dear Ava, this is going to sound weird but can you turn a hookup into a friend. Let me explain. I’m all about dating cougars. I’m twenty-eight and I met an older woman at a bar a couple of months ago. We had sex that night and a few times since. Sadly, it hasn’t been that great. Here’s the weird part: when we’ve gotten together (before the sex) we’ve had a lot of fun. We’re both super athletic, so we did some hiking and rock climbing which I’m used to doing with guy friends, so that was cool. And she’s super intelligent and makes me laugh, both of which I think are sexy. Is there some way to back off from the sex and keep her as a friend or is that just crazy thinking?
A: You’re right, P. This is a bit strange. I’m used to men asking how to turn a friend into something more, not the other way around. The reality is not every mature woman you meet is going to be off-the-charts explosive in bed. You’ve got things in common with this woman, she’s intelligent and funny (both of which you describe as sexy) – all things that lend themselves to compatibility, but you don’t mention your attraction to her physical beauty which must be present for desirability. I think compatibility and desirability both need to be present for great sex to happen.
You don’t give much detail about her feelings towards your relationship, if you even know what they are, but seeing as you’ve been on more than a couple dates, I assume she’s interested in exploring the possibilities. To tell a woman who you’ve already been sleeping with that you just want to be friends, well… not so easy. Even us confident cougars will feel jilted and there’s not much worse than having your sexual prowess or attractiveness be called into question. This will likely make her feel self-conscious of her age and feel like she’s been put into a “motherly” role. Do you really need her as a friend? Older women don’t usually want younger men for buddy outings, we want the physical relationship, and I don’t mean rock climbing.
Either giving the sex a chance to improve (Is she holding back for a reason? Maybe she wants you to dominate? Are you inexperienced? Is there enough dialogue during sex?). If that just doesn’t work, be honest. There won’t be much to lose at this point; she’ll either tell you to F off or she’ll be into the “friend without benefits” scene.
Love to hear how this one turns out! Readers: any similar experiences to share?
Need advice on dating, relationships, or sex? SUBMIT YOUR QUESTION HERE, and who knows, you may appear in the next Cougar World newsletter. -xo Ava