Dear Diary: Jessica Falls For An Older Man

In honor of Dear Diary Day, brave Frisky staffers share their most mortifying diary entries. Share yours in the comments. We promise not to laugh.

This is from Sept. 29, 2006. I was 22 years old, working as a newspaper reporter in Connecticut, and I was in love with a 37-year-old man. He worked at the magazine I had interned at the year before and had become a mentor. Names have been changed to protect the guilty.

The night before last, I slept with Dan*. I finally had sex with someone who I loved and who cares about me and who treated me the way I should be treated in bed. Intimate. Sex has only been badly intimate before; I have often started to cry when a guy is inside me because I don’t like it. But this felt different, like we were sharing.

I don’t feel like it was a choice to do this, in the sense that I’m too far in this emotionally with him to stop how I feel. I stopped being in control of that awhile ago; I really do feel like it’s not in my control. That way, it’s almost easier — I’m just doing what I want to do because this is how I feel. The flip side, of course, is that its a fact that exists, that won’t go away, even if it might be good to.

I don’t know what would be good anymore — I’m too, too far into this to see objectively anymore — but I know I can’t choose to stop caring about him or loving him now. But then, what do I do? I know — I know — that he can’t be my boyfriend, practically. It just doesn’t fit. That was clear two weeks ago and became clear again the other night. Our lives our at two different places; I would be a kid to him, a guest in his house, and not an equal. It’s hard to explain because we’ve become so close, we care for each other very much, you’d think the physical/age difference would matter but its not [sic], but something doesn’t fit. Not with me 22 and him 37. I wish it didn’t exist but its tangible.

Where that leaves us, I don’t know. Where that leaves me, I don’t know. We drift apart, I guess.   ….   He severed a tie, an artery pumping the fantasy into my head, on Monday night. Monday night is a stupid night to tell your 37-year-old lover that you are in love with him.   …   What’s the worst that can happen when you tell someone you love them? I found out one version, one answer to that question, Monday night. … Arguably the horrible fight we had [after I said “I love you”] — fight? dispute? entanglement? drama? — made us closer. But definitively what I got out of that three hour-long, wrung out conversation was he won’t be my boyfriend and he didn’t say “I love you” back.