Will he be open to a relationship?

I guess we'll do Love Letters?

Hi Meredith,

I had to write in after reading "Should I not have asked about our relationship status?" I, like the letter writer, have long struggled to find a balance between going with the flow in a new relationship and needing things to be defined so that we are both on the same page. I have a habit of falling for/dating guy friends and my current situation is no exception. The guy is nice to me and we are both very attracted to each other. He has made it clear that he wants to be with me, but told me that "the door wasn't opened, but it wasn't closed" to the possibility of being boyfriend and girlfriend in the future.

We have known each other for a year and a large part of my concern is my past experiences dating friends. My dating history has shown me how badly relationships/emotional entanglements with guy friends can end and I want to make sure that both of us could see a future with the other person before jumping into it. Dating without knowing that the possibility of a future is there means that I could lose his friendship and it could mess things up without our mutual group of friends.

I go back and forth between wanting to be happy in the "now" and preparing for the future. I know that I over-think things but I'm worried about being with him and then having him realize that although he wants to be with me, he doesn't want a girlfriend in general. I don't know if I want him to be my boyfriend, but I know that I want that option there. Otherwise, it feels like the relationship would have a shelf-life of sorts.

Making things more complicated, he is newly unemployed so he can't even fathom the future beyond getting a job. Should I just go with the flow and be with him or should I wait until he has a job and talk to him again?

– Trying to be happy, Hyannis

"I go back and forth between wanting to be happy in the "now" and preparing for the future."

Are you happy in the now? It doesn't sound like you're very happy. You're already sweating this situation and feeling a bit ... put off. Meanwhile, he's in charge of some magical door that's not open or closed. If you're ready to meet someone who's interested in investing in a relationship, this "friend" might not be the guy for you.

You've given this guy all of the power, but this is your choice, too. You're supposed to be trying to figure out what it's like to date him and whether he's worth your romantic energy. Are you asking yourself these questions? Or are you simply focused on whether he'll want you?

You can't ask him for answers about the future. No one knows how this will play out, even if you're both in it for the same reasons. But it's fair to want to be with someone who's open to more if things go well. That's the only guarantee you need. If it feels like you're just orbiting him, waiting for his decision about you, it's time to walk away.

Readers? Is she having fun? Should she be with someone whose door isn't quite open? How can she stop herself from wanting guarantees? What about the friendship? Help?

– Meredith