Afraid to break up with him

Hi Meredith,

I am a huge fan of your column and this is my first letter. I am 27 and my best friend/boyfriend is four years older than I am. We'll call him Henry. I love Henry so much, but things between us seem to be going down the drain. We've been together for almost two years. But about a year ago we separated for a few months because I felt our long term goals didn't match.

Lately I've been thinking about both of the guys I dated during that separation and how much better they treated me. They asked me what I wanted to do when we went out and they did little things to show that they cared about me physically and emotionally. Henry has always done whatever he wants to do and I have settled. When I have felt strongly about things I have kept quiet about them for months -- sometimes 6 months. I just tend to do everything his way. He also criticizes me constantly. I recently lost my temper twice and we had a fight about my roommate who was annoying me and my driving. I think I lost my temper because I'm fed up with his general behavior. Things have been this way between us for six months or so but we have both been busy with work and just content enough to stay together. I don't think he likes someone else but I'm sure he fantasizes about other women/things. I think he feels that he is tied to me so he shouldn't be expected to do other things that make me happy.

Overall he is a wonderful person and I even love his family. I would love to marry this person further down the road, but it seems like he is more independent than I am and critical. I love him so much and have tried to give him what he wants, but I don't know if I can take it any more. Is it possible to change this pattern with Henry and did I set myself up for it to end this way? Should I do the scary dating thing again? I know it is also a rough world out there. The upside to all of this is all of the frustration I didn't take out on Henry I spent at the gym for the past 4 months! So I am in the best shape of my life, but the person I'm with hasn't even noticed. Thanks!

– Holding on to Lost Expectations, Boston

You want to marry this guy? What? Please read your letter a few times -- out loud.

The part of your letter that interests me most, HOTLE, is this question: "Should I do the scary dating thing again?" I assume that’s why you're staying with good-old Henry. Dating was frightening. Maybe those nice guys ended relationships before you were ready.

Dating new people is scary, for sure, but not as scary as wasting time with someone you know isn't right for you. You don't want to marry Harry. You don't even want to keep dating him. I don't know if he's fantasizing about other women, but you're certainly fantasizing about the men you dated during your break from Henry.

You're not dating Henry's family. You're not dating the fictional Henry of the future. You're just dating someone who isn't making you very happy.

My advice is to get back out there with your awesome gym bod. And again, if you're feeling insecure about doing the right thing, read your letter aloud. Over and over.

Readers? Why is this difficult for her to see? Or am I wrong? Can you tell her something to make the "scary world out there" less scary? Discuss.

– Meredith