I’m at a bit of a loss. I met a guy that I really like at a nudist resort of all places. I didn’t realize at the time just how much I was falling for him. He was trying to be more in the beginning but I missed some very obvious signs. Hindsight is 20/20. I’m incredibly guarded after growing up in an emotionally abusive household and am still dealing with some trauma after being raped a few years ago. By the time I realized how I felt about him, he surprised me by telling me he had a girlfriend. He and I run in the same kinky circles and I ran into them at an event. I actually got a horrible sinking feeling in my stomach which I didn’t expect. I never told him how I felt about him. I’m happy that he is happy with her but it hurts, nonetheless. He matters enough to me that I would be content keeping him in my life even if it’s just as a friend. My question is should I tell him how I feel and risk losing him altogether or do I let him be happy with his girlfriend and not tell him that I fell hard for him? I know he might not reciprocate my feelings. That’s okay if he doesn’t, but the not knowing I think hurts more than the truth would.
—Hopeless Romantic Nailing The Hopeless Part
If the not knowing hurts more than losing his friendship would—if not knowing whether you had a shot with him and blew it—then you should tell him how you feel (or felt) and express regret for missing the obvious signs and disappearing on him. And as painful as it might be to hear that he wouldn’t want to be with you even if he were single—and that’s the worst-case scenario—you will get over it and get over him. Best-case scenario, HRNTHP, he had no idea you were into him, he’s not serious about the new girlfriend, and he’d rather date you. Less-than-best-case scenario, he might be willing to date you if 1. things don’t work out with his new girlfriend and 2. you’re still single at that point. In the meantime, don’t pass on any other opportunities that come your way and be courteous, polite and non-toxic when you run into them together at kinky events.