Dear Sibyl, This summer, one of my best friends from childhood contacted me. Actually, he was the first person I ever Loved. As a teen, I hid my feelings from him for five years. Finally, I told him how I felt in a letter, and said that if he didn't feel the same we shouldn’t continue to be friends. I didn't hear from him again until this summer---fifteen years later.
When I heard from him, I was both excited and wary. It was great to have him back! At the same time, he was newly divorced after being separated for a year and clearly looking for something. He said that he had a crush on me all those many years ago too, and that he had thought about me many times. He started to talk about wanting to come visit. I live over 600 miles away. His tone became more and more romantic, and it was around this time I decided to do a reality check.
I didn't say I wasn't interested. On the contrary, I was very interested, but I said that if he was going to keep talking romance, I needed to see him. I told him that I really want children and a family, and that if he wanted to get together I would need him to be open to exploring that possibility with me if things went well.
He responded that he cared about me, but that his relationships usually happen more 'organically'. I said I understood and was sincerely grateful for his honesty. We both said we were still very much interested in maintaining the friendship.
I didn't hear from him after our conversation for four months.
On Christmas, he reached out. Although my feelings were mixed, I was mostly happy to finally be hearing from him again.
He dated someone briefly in the intervening time but is once again alone. A few months ago, he was checked out by a doctor and learned he is sterile. He bought a house in order to move toward a place where he can have a wife and children. He knew he was sterile when he bought it, but he hopes to have a family through non-traditional means. He was not in a good place on Christmas, because he had just spent the whole day around family with lots of little children. He was feeling lonely and sad. I doubted when I hung up the phone that I would ever hear from him again.
Since then, he has apologized several times for being a bad friend to me, and the two of us have been communicating almost every day, texting or emailing. It has felt good to have him back in my life.
My love life has been complicated recently, and I let him know that the first time we talked. For the first time ever, I’ve had a Friend with Benefits. My FwB is great, but I always knew he was moving away. In fact, FwB just left this morning.
The longer my old crush and I talk the more I realize I have major unresolved feelings for him. In fact, I have been unable to climax since our initial Christmas conversation. The one time I successfully came, it was because I was concentrating really hard on pretending I was with Old Flame instead of with my lovely FwB. This has never been a problem for me in the past.
Mostly, boundaries with Old Flame have stayed platonic this time around, but last night, on the eve of my FwB's departure, I texted that I was considering spending the next six months in celibacy. Old Flame texted back ('jokingly") that I should visit him so he could “knock the bottom out for me instead”. We flirted with each other and with the idea of me visiting.
I know this situation is emotionally precarious. I really do want a family and a partnership, but after years of searching, I’m also feeling exhausted. I want to have fun. I want to have sex, hence the FwB. I want romance to just happen for me the way it seems to be happening for ALL of my friends without having to work to meet that someone special.
Even more powerful than these needs for sex and fun is the feeling that this man still has lessons to teach me. Maybe he's just going to teach me more about heartbreak, but there's only one way to know for certain. I want to find out.
I want to visit. I want have sex with him, but I don't know if the flirting is genuine. If it's not, I definitely need to ask him to stop. At the same time, I'm tired of being the boundary police, the one who has to bring up all the serious stuff. I’m also dreading bringing it up since the last two times I brought it up he completely disappeared. If it happens again, do I keep letting him back into my life? Our relationship has meant so much to me over the years, I don’t want to cut him out. How do I even start this conversation? Again?
Sincerely, Deja Vu
Dear Deja Vu,
Sweet baby jesus, you have a LOT going on here, girl.
The first thing I need to point out here is that you have not seen this person in fifteen years. Fifteen years. I know he seems quite attractive and interesting over text, email, and the phone, but things can be very different in person: is he comfortable in his own skin? Does he tip waitstaff well? Is he a road rage driver? Can he dance? These are things you'll never know on g-chat, and could be deal breakers.
The thing is, I am getting the sense from your letter that nothing would be a deal breaker for you. You want to correct this past hurt that you’ve held onto for all these years, and you’ll jump at any chance to do so. It was not too much that when you expressed your desire for kids, he disappeared, or that he came back saying that he's sterile, then vanished again. So far, this "relationship" is completely on his terms, and you are hanging on his every whim, like. . . well, like a teen with their first love.
It's like you took a snapshot of him at that time, over a decade ago, and you're in love with a photograph, not the real guy. You're dying to get back that hormone fueled fusion the two of you shared, which, even then, was rooted in you pursuing and him distancing.
I understand your strong desire for a relationship -- the part of your letter that was about your longing for love, fun, and sex was the most relatable piece. However, I have to be the un-fun boundaries holder that you no longer wish to be.
Reality is, none of your friends' loves are as easy as they seem from the outside. Love is always messy, fraught with doubt, and everyone eventually has to do massive amounts of work to come to a good place with the other person.
To sum up, dear Deja Vu, Step One is to meet this guy. Go ahead, have sex with him, get all your curiosity and teenage dreams fulfilled. However, if there is even a glimmer of the pursuer-distancer pattern between you in person that you've established across the miles these past few months, run, Lola, run. You don't want to spend your life offering him things just so he can turn them down.
I know you want a relationship with a long-term partner. However, don’t settle for Old Flame if it turns out he’s really just looking for a flash in the pan.