Advice dating old friend

In a few days, I’m going to Cuba on vacation with a guy I’ve been sleeping with for eight years, but whom I've never once called my boyfriend.

We live on different continents, but inevitably, a few times a year, we find each other somewhere in the world, have a few days of romance, and then go our separate ways.

Even if your friend claims to not care about witnessing affection, make a point to tone it down while around him.

There's nothing wrong with holding hands or kissing, but reconsider going into a full-on dry-hump session while you're all sitting on the couch together watching We're saving the best for last, except this one is "best" in the sense that it’s the best way you’ll get excommunicated by your group of friends forever if you do it.

When I met him, he was 45 and charmingly grumpy, and he would always tell me: “Sex is so perfect. ” I’d go over to his apartment for a couple hours in the afternoons, we’d have sex (soberly, which meant I could actually cum), and then afterward we’d drink tea and complain about stuff. There were times when we saw each other frequently, and other times when things dropped off for a while, usually because one of us had a partner. It felt like we had entered this secretive bubble of transparency—we were emotionally intimate, yet free of the burden of jealousy and ownership.

And sure, when he would get a girlfriend I would be a little bummed out—I’m (unfortunately) not a sociopath—but it didn’t cause me to spiral into an emotional cyclone the way I would have if I’d been cheated on by a boyfriend. We could spill our guts to each other because we didn’t have anything to lose.

This arrangement would generally be called a friend with benefits, or a fuck buddy, or a romantic friendship, or perhaps even a relationship—with “no strings attached.” But let’s be real: There are always strings, aren’t there?

The best thing is to be honest with yourself regarding the nature of your feelings. " The reason I went after TWO of my BFF's ex-girlfriends is that I really believed I would make a good match with both women.

Don't mess around with your friend's ex behind his back.

That's a shitty thing to do and they will almost always, inevitably, find out.

Don't risk everything for the possibility of piping-hot sex. "Are you making them out to be an idealized version of what they truly are? Let an honest assessment of your feelings factor into how you decide to proceed.

Sex is fantastic and all, but there are so many other people (who "Are you romanticizing the person? "People often idealize things they only see in ‘highlight reel’ form.

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