How to have the "what are we" conversation?

Hi all, this is my first post here so I thought I'd make it about my biggest current love obstacle. I'm in college and met a guy last year through a friend and we have been friends since. At first, we didn't really talk much and just saw each other when we were with our mutual friend (he had a girlfriend at the time and I wasn't even interested then.) We are both pretty private people and do not let people just come and go into our lives very often so when that mutual friend moved away and his girlfriend broke up with him all during the same month, we started to hang out more. I have been sleeping with a different guy for the past year as a friends with benefits and he had no idea. The (not fwb guy) guy this post is about has taken me out to eat on occasion but most of our time is spent just watching tv. We are getting ready for a weekend trip together to visit another mutual friend soon.

Before I get too far ahead of myself, here's a few necessary details... he was snooping through my computer once and came across my stash of nudes which weren't exactly all vanilla so he knows that I like sex and am open minded. We slept together once a few months later after he saw some fading hickeys I didn't notice from my fwb, a fun day together, sexual tension and awkwardness. I'm not sure if the hickeys had anything to do with the timing . We have texted each other about hooking up again but it never leads anywhere despite seeing each other at least once or twice a week. When we're together I can feel the tension and we both get kind of awkward. It is really time to sit down and talk about our feelings and clarify some things but I just don't know how. I have some personal issues (I am bipolar as well as have a ton of baggage) that I've never directly told him but feel that I need to since they always impact relationships. I really do want to get closer to him but am not sure how to go about it.

I've never had a serious, long term relationship and am not even sure if I want to have one with him and I assume he realizes this but I want to know where he stands. If anyone could offer some advice it would be much appreciated!

If you can find the right moment -- somewhere relatively private -- preferably not too much alcohol involved, maybe before or after some kissing -- tell him you like him. Make sure your tone of voice conveys that you LIKE like him. . . romantically but don't spell it out. Guage his reaction. If it's positive, say something else along the lines of "I think we've got something good going here." See what he says.

If his reaction isn't so great, figure out whether you want to carry on as is or you want to change things.

Make sure you know what you are doing with FWB guy before you dive into a relationship with this guy.

The timing is important. Make sure he can't hide or run away from the subject, but don't push it too much. Casually slip the subject into the conversation and gauge his reaction. There's no shame in asking what he thinks of you or where he sees this going. If his answer is kinda dull don't make too big a deal out of it. Some people get excited about relationships slower. Good luck!

Hi ivyqueen, do you think he likes you?

Put him on the thread. I'd like a word with him about you since you're not being honest with him about anything about yourself. You should let him know what he's getting into (if he's wanting to get into you for more then another FB)

In future you might not have to feel so awkward (or as if you have something to lose) if you are upfront about yourself before you have sex and if you wait to have sex with someone that has shown you that you are more then a platonic friend. Now, currently... you have two FWB's.

As for your actual question: Start out by telling him about yourself... then gauge how he accepts/reacts to that. You don't owe him anything at this point but your honesty.

I've always had this conversation while driving. You're both stuck together with nothing to do but talk, so I think it's a good strategy if you want some answers.