ascending friendship?

[kanaliket]

Hello!
I have this friend who I've crushed on for a bit, and I kind of want to be more intimate with him. Only recently did I get a chance to say I'm interested. The thing is, we planned a meet up after that, but the day of, I got so nervous that three hours before I chickened out and said I had "volunteer work" and couldn't make it.

I'm not sure what I want anymore. I really want to just be close and kiss, but I'm also afraid that won't really happen and it would just be boring because I'm not as good a conversationalist as his other friends.

Then that got me wondering whether I even trust them enough to be intimate if I'm too anxious to show up under the premise of it. I don't even hang with this particular friend all that much, we barely text, and I mainly have a crush on this other girl but I know she won't return my feelings because we're both girls.

I'm just so confused, how do you advance a friendship to a relationship, and how do you know if it's right to? (And how do you back out politely if it's not right to?)

[Sam W]

Hi kanaliket,

It can definitely feel tricky trying to determine if you want to move from a friendship to a romantic relationship with someone. Part of that is because it has so much to do with the specifics of a given situation. You've actually already taken one of the harder steps, which is being honest with the friend who you're interested in exploring a different kind of relationship with. It can also help to look at the foundation and dynamics of the friendship before taking the leap into a romantic relationship. If communication comes easy, and there's a lot of trust, comfort, and affection with each other, then that's a promising starting place. But if those things are kind of lacking in the friendship, that may not make it the best place to introduce romance. Does that make sense?

In your case, it sounds like you're having some second thoughts about your guy friend. Can you tell me a little more about what those nerves you felt the day you were supposed to meet were about? Were they just general anxiety, or were you worried about something specific?

With your other friend, is there reason you say she won't reciprocate your crush is that you know she's straight?