How Do I Find Out Where This Relationship is Going?

Dear Sara: I met a guy in late spring last year. Shortly after we met, he asked me on a date. 

We’ve been going out at least once or twice a month since then. When we do go out, we seem to enjoy each other’s company. He’s met some of my friends and I’ve met his. While he initially asked me out several times last year, towards the end of the year and through this year thus far, I seem to have become the pursuer. I feel like we connect and I’d like to move our relationship along. I obviously have feelings for him, but I’ve have had little movement on his part to take our relationship “to the next level” so to speak.

I have been contemplating telling him my feelings, but of course there’s the possibility of rejection. Another part of me is frustrated because I think if he liked me as more than just a friend, he would have told me. While I have received advice to just enjoy my time spent with him, and to not worry about who asks who out on a date, I continue to go back to the idea that I need to be honest with him and tell him how I feel. I realize that I might lose him as a friend if I am honest, and I know this will be hurtful, but I can then ultimately move on— slowly but surely. – A

Dear A: It’s easy to get tripped up in these kind of situations—I know I did. You’re involved with someone, but things don’t seem to be moving along as you’d like. But you’re afraid to say something because you don’t want to seem needy/weak/desperate/etc. Many of us have been conditioned to think that asking for clarification on a relationship status puts us at a terrible disadvantage.

I would suggest asking this question from a position of power rather than weakness. The overall tone should not be “Do you like me?” or “Will you ever want to be serious with me?” But instead, “I need to know where this is going, if anywhere. I really like you and want to stay friends no matter what, but I need to know if there is potential for a relationship here, because if not I need to move on.”

Or something to that effect. The idea is not that you’re looking for his approval. You’re trying to plan your life, and you’re entitled to some clarity from him on what your relationship status is.

As you say though, there is the possibly of rejection. From the sound of your letter, it sounds like you have already taken the important step of accepting that you may not hear what you want to hear—and you also recognize that that is preferable to being strung along.

So that’s great—you’ve already taken a key step to starting this conversation from a position of strength. Once you accept that the conversation may not go the way you want, you can also get clear on the fact that, however painful this may be, ultimately you.