Hi Meredith,
I have a sort of strange situation I need help with!
I am a recently engaged 31-year-old. Although there were a couple of “bumps” along the way, I think our relationship is the strongest it’s ever been and I’m excited about our future together.
Having said that, one of the issues we did encounter some time ago was that my boyfriend (now fiancé) had a female friend (who happens to be an ex-girlfriend) I never knew about. I was never a controlling, jealous, needy girlfriend. In fact, I think the “freedom” I gave “Jim” was what caused this issue in the first place. I was very confused why he would hide this friendship. They would occasionally get dinner and catch up. I guess she has a boyfriend, as well, and their friendship was completely platonic. I’ve come to believe that, but a scar certainly remains for me. When I found out about this girl (I snooped through his phone and saw a couple of texts – nothing bad, nothing sexual), I was devastated he would hang out with someone behind my back- especially because she was an ex. I assumed they weren’t just “catching up.” We went through couples’ therapy and he no longer speaks to her and has really made a 100% effort to be truthful and non-deceitful. Weirdly as it seems, that event seems to have made us stronger, even though the level of trust will never be the same.
However, I feel I needed to tell that story before I got into my present problem. Before Jim was in the picture, I met a guy online. This was in 2004. We never dated and never even met. I guess we both sort of chickened out about meeting. However, we have remained close “e-mail” friends for the past five years. It is strictly platonic and it is not sexual at all. It’s hard to describe, but we can share problems/stories with each other and trust that other will not share with anyone else. We write back and forth at work and that’s it. Nothing at night, nothing on the weekends. During the work days we email back and forth a lot — almost every day.
The problem is that I feel guilty I’ve never mentioned him to Jim. It’s embarrassing to tell him I met him online and I feel like it’s hypocritical because it’s me hiding someone just like he did. At the same time, I feel it’s different because we have never dated and do not hang out face-to-face.
Meredith, am I terrible hypocrite? I am wondering how to tell my fiancé without ruining my relationship?

– Hypocrite in Boston?