Feelings for my friend

I think it's time for some updates.

Former letter writers, I'd love to hear from you. Tell us how it all worked out -- and make sure you write to me using the same email address you used the first time around (that way I know it's you). Also tell us how we were helpful/not helpful.

Dear Meredith,

Perhaps you and your readers can help me. I'm in love with one of my best friends and I don't know what to do since we have an emotional roller coaster of a past.

The background: Rachel and I met through mutual friends about a year ago. Very quickly we grew close and became an important part of each other's lives. I'm 26 and have a very respectable job in my field, while she's a few years younger and finishing up school after a few years off. Since our friendship began, there was always kind of a back-and-forth between us being interested in one another. It got to the point where we were practically dating, although she was kind of oblivious to the meaning of our actions -- spending a lot of time alone together, confiding in each other, texting for hours on end (we never did sleep together). Finally I gave her an ultimatum: we have to act on these feelings or we need to take a break as friends because I wanted more. She said she wasn't ready to be with me (though she wanted to be and cared about me) because she had to figure out some stuff about herself and she was scared of a relationship going badly and subsequently ruining a close friendship. We were both crushed by this, but it had to happen. So I cut her out of my life completely for a while.

Shortly after this, I found out that she started going on dates and sleeping with a mutual friend, John. My sadness about the state of our friendship turned into anger and hurt. She could act on her feelings for John but not me? Especially when EVERYONE that knew both of us told Rachel she was stupid for getting involved with John because I'm a better catch than he is in every possible way. I was so angry I never intended to speak to her again. (The thing between Rachel and John ended quickly to no one's surprise).

About a month later, I finally lost the energy to be angry and because we have mutual friends, I asked Rachel to talk. My original intentions were to reconcile so we could at least stand in the same room without it being awkward. The talk ended up going better than expected. She acknowledged that she hurt me and that she should have acted on any feelings for me instead of putting me in that weird gray zone. I told her we could be friends again, but that she would have to earn my trust back, and that if she ever hurt me like that again I would be out of her life forever. She was blown away by how forgiving I was and promised to never take my friendship for granted again.

Presently we're back to being close friends. The only difference is that I don't confide in her because of the lack of trust. However, the feelings I had for her are slowly coming back. I think about her a lot, we talk a lot, and we see each other often. She's not involved with anyone right now, but I can't stand the thought of her getting involved with someone else at some point. I told myself (and her when we reconciled) I would never pursue her again, and I feel like talking to her about this would ruin the friendship we just got back. I tried using dating to get over these feelings, but it's either a one night stand or doesn't go anywhere. I don't know how to view our friendship without any romantic thoughts.

– Lovesick Over A Friend, Boston

I don't know why you're so desperate to maintain this friendship, LOAF. You know your goal here. You say at the beginning of your letter that you're in love with Rachel. You want to be her boyfriend.
Instead of punishing her for making a decision that hurt your feelings, tell her that you've come to terms with what happened and that you're ready to try a romantic relationship. You're single. She's single and in a better place. What's stopping you? Your pride? Your fear of a second rejection? Your need to call her a friend when she's obviously more?

I'm not saying that she's totally innocent here. It sounds like she led you on quite a bit, which isn't very nice. But she didn't cheat. She's always been honest with you when you asked her direct questions. She just made you feel bad. That's forgivable.

You've basically reunited for a do-over. You can use that do-over to force a friendship or you can ask for more and see what she's capable of this time around. If she says no again, at least you'll know how to set your boundaries.

Readers? Why did he tell her that he wouldn't pursue her again? Does she want to date him? Should they try a friendship? Should he ask for more right now or wait to see how this evolves? Help.

– Meredith