Dear Wayne and Wanda,
I met “Jim” several years ago. He had just divorced after a brief first marriage. We really hit it off but I was about to move out of state, so we didn’t let things continue. Not long after, he met and married his second wife. I always wondered if moving ruined what could have been an amazing relationship.
I recently returned to Alaska and Jim reached out to me to let me know he’s getting divorced again. He asked if I wanted to catch up. So we met up for drinks and it was just a wonderful night. We had tons to talk about. He was very open about why his marriage ended — like wife No. 1, she was unfaithful. I felt like the chemistry was still so strong.
So when he asked me over, I went. Maybe I shouldn’t have. Part of me wanted assurance he’s truly separated and there weren’t signs of his wife still living there (there weren’t — she seems to be out of the picture). I didn’t stay over because we both had early mornings. I went home so happy but woke up to a text from him saying that he had fun but he’s “working through things” and not sure what he can “handle” right now.
I don’t want another friend with benefits. I want a serious boyfriend and eventually marriage and kids. Have I ruined things with Jim? Can I fix this?
In the travel world, there’s something known as a “shoulder season” — essentially the downtime between peak and off-peak times of year. Hate to say it, but you’re currently the embodiment of Jim’s shoulder season; you aren’t just a shoulder to cry on, you’re also the person he apparently retreats to when he needs to rebuild his self-esteem and maybe have a little fun to remind himself he’s not just the guy who gets cheated on and maritally abandoned.
If you’re really serious about this guy, take a break. He’s going through a divorce, which is a massive transition. Even when people know it’s the best route forward, it’s extremely tough, and it can be incredibly emotionally disorienting to figure out next steps. You don’t want to be part of the messy transition that Jim will always remember as challenging and traumatic; you want to be part of his bright, fun future!
So don’t sleep with Jim again, and don’t let yourself be the therapist. Tell Jim, because you truly care about him and have hope for what might be, and because you care about his healing, you are going to step away — and when he feels ready to date, you really hope he will give you a call.
In the basketball world, there’s something called a “rebound” — essentially when someone misses a shot the ball is suddenly up for grabs. Hate to say it, but your man keeps heaving up bricks and you are the most aggressive and thirstiest defender around to go after the loose balls. You’re also the nearest in proximity, which increases the rebounding percentage for a gym rat like Jim.
This player’s a free agent whose career is on a Hall of Fame trajectory. Don’t be another statistic and don’t sit on the bench waiting to get called into the game.
Tell Jim to go ahead and work through things because you’ve already got things figured out: you want a stable relationship and a future that includes a family. That might not be a slam dunk for a single trying to find an all-star, but it’s definitely better than taking a shot with Jim, who is clearly an air ball.