My friend and I both turn 40 this year. We used to fool around and have sexual experiences together when we were 16-22ish. Grew up together since five years old. A several year intermission around 12-15 because life’s like that sometime. At 23 I became involved in parenthood (now 2) and having a spouse. Not much longer after that my friend too became involved in a relationship, now with 3 children. Fast forward nearly 18 years later we’re still good friends. Though I’m not sure about these feelings. I want to let him know I still love him, more than a brother. If there’s ever a way for us to be together and he’s willing to entertain it I believe I would take the chance. Find out too if there ever was a chance before getting into our current relationships that we could have tried if I asked. I’m any case I want him to know yet I don’t want to put my friend in an awkward position.
When you have that much history with someone, you probably *do* need to resolve your lingering regrets and hopes, otherwise they'll follow you to the grave. You're lucky to still have ties with someone who was that close to you - nowadays, by the time people reach their 40s (and with families), their social circle typically shrinks and they lose most of their connections with childhood. If your friendship has survived intact this long, I think it's probably strong enough to weather the possible awkwardness if you bring up the, um, past... As for how to raise the topic, that's tough to say. All I can suggest is, perhaps, to not put him on the spot ? For example, you could ask casually, "Do you remember when we used to do such and such ?" or "Do you ever think back to the days when...?" You wouldn't be putting any pressure on him to resume intimacy, and you could gauge from his response who much further you can go. One thing about middle age is that people also get really nostalgic. If he cares about you as much as you do about him, it will be difficult to hide, once you open the door.
Actually, opening that door isn’t likely something I’m ready to do. It would definitely take more to break our relationship as is. We are still intimate on the level of “brothers” even more so than my blood relatives. It’s hard not to feel that when we’re having great big hug and I have to restrain from trying more. Otherwise that is excellent advice, thank you.
I hear you. The upside of letting the past stay in the past is that it remains golden. You'll always have those good memories to fall back on, which is not necessarily the case if you aim for a sequel in the complicated present. But good luck to you if you change your mind !
