falling for my roommate... oh no, this ain't good

[Jowee]

So I am falling in love with the same woman again... and this time we are roommates. This is going to be a tricky space to navigate (and by navigate, I *mostly mean escape). Anyway here let me break down all the factors.

 

- I have known this woman for 6 years.

 

- We met in college (in 2009) when I tried asking her out, which she let me do... but it didn't go anywhere and led to rejection. I acted like a whiny brat about the rejection, and was basically a giant tool... this strained things.

 

- We had a very rocky on again off again friendship for a few years.

 

- At the time and for a few years after, we were both very emotionally insecure people (although for other reasons). If anything, this is what caused us to later begin to build a strong friendship. I was definitely the shoulder to cry on and she was mine... kinda pathetic actually.

 

- She had been in and out of several dead end relationships, and then met a guy who she later left. She told me her simple reasoning was that she thought she could do better than him. She has stated that she regrets doing something so immature. She hasn't dated seriously since then (as far as I know) and that was years ago.

 

- In the last 2 years we talked practically daily and our friendship has solidified and strengthened.

 

- I moved across the country one year ago and of course kept in contact with her. A couple months ago she decided she wanted to move out to where I was now living. She likes the area, and one of her brothers lives out here.

 

- So I agreed to let her live with me, so she moved in and now we are roommates.

 

 

Here is the thing. Our friendship has completely changed since she moved in with me. We went from being rather solemn and serious friends, to be very very close *best friends. I have never had so much fun with another person in my entire life... seriously its uncanny.

 

We hang out all the time, we still have our own separate lives of course. But we spend an inordinate amount of time hanging out with each other. We like the same music, same types of movies and TV, same types of outdoor activities, etc... we have senses of humor which match perfectly. We are both really goofy people and do and say the most random things and it almost always results in grinning, smiling and laughing our asses off.

 

The amount of laughing and smiling in my life has grown 50 fold since she moved here. Anytime I am with her, we seem to have a blast. We are also always teasing each other but it is always received well and has led to many "inside" jokes between her and I, which get dropped all the time it seems.

 

She and I are always texting each other silly things, or just to say hello and see whats up. I get texts out of the blue just because she was thinking about me, just wanting to know how things are... even when it hasn't been very long since we both went about our days. Between 10am-1pm I am almost guaranteed to get a message from her, asking how my day is going. Of course I do the same to her, its about a 50/50 split of who contacts who first.

 

We are patient with each other, we respect each other, we care about each other, and most importantly we genuinely appreciate one another. We never fight... ever, although we do have these funny bickering moments where we sound like we are effing married.

 

... I am falling in love with her, this is not the person I met in college. This is someone entirely new who has captured my heart and my mind. And to be frank, I am not the same person either, I am older, far more mature, emotionally stable and happy.

 

Unfortunately there are some big issues holding me back from telling her how I feel.

 

1. I don't want her to think I am taking advantage of the fact we are living together or even worse, think I engineered this situation (I surely did not, I did it because I needed someone to help me with rent).

 

2. We share a very small space with little privacy and I would hate to creep her out.

 

3. I don't want to repeat the first rejection... still to this day I am not positive why she rejected me the first time. Just because I have become a better and more complete person doesn't mean I am now some how more attractive to her (although I might be).

 

4. Comparatively, she is far more attractive than I am... I am maybe a 4/10 where she is a solid 9/10 (a 11/10 to me... but I am biased). I am not ashamed that I am not that attractive and I rarely think about it. But I am being realistic, to deny that physical attractiveness doesn't play a part would be deluding myself.

 

5. Now here is the really really iffy part. So about 2 years ago I came out as being transgender and am in the process of transitioning from male to female. I am still along way off from completing that process but she knows it's happening. I don't think she is bisexual, but I have never asked and I think if I did ask that it would be obvious why I am asking. And even if she is bisexual, she may not be ready or willing to deal with the stigma of dating a trans person... she is self conscious enough as it is, I think she may end up getting embarassed of me and not be able to handle that on top of her insecurities. Although I may be vastly overstating that insecurity.

 

Anyway thats enough for the first post. I am looking for opinions on the situation and suggestions on what I should do (right now I plan to keep it to myself and do absolutely nothing different than what I am doing now).

[Tressugar]

For your own self preservation don't do it. Don't cross that line. Don't fix what isn't broken.

[Jowee]

Well of course it isn't broken... but it also could be an amazing relationship waiting to happen. If she doesn't feel the same I doubt it would ruin our friendship or anything like that but it would make things awkward for awhile (especially considering our living arrangement). I actually have a date lined up with another girl this weekend so its not like I am holding back my love life for her. But if I could be with anyone, it would be her.

 

I guess at this point the three big things holding me back are the fact she rejected me in the past, the possibility of embarrassing and making a fool out of myself, and finally the whole trans thing (gender complicates EVERYTHING).

[littleplanet]

Wow.

That's a helluva story.

I'd say if you two are that tight....somewhere down the line your friendship can stand a little truth-telling.

You may be surprised at how well she takes it.....although that might not necessarily mean anything fundamentally changes in your relationship.

 

You have changed obviously in your feelings for her - but has she given you any kind of sign that hers have for you?

 

I haven't a clue what advice or even opinion to offer on the gender thing. (That's just a bit too much of a mind-warp for me.......but don't take that the wrong way. One of my best music jam buds is a trans.)

 

But back to the obvious: it's a classic.....a friendship like what you described can often be the kind of thing that smart people don't want to mess up by adding romance. Especially when it's that special.

 

So be creative. Start up a line of those patented "in jokes" you do so well - spiced up with a little bit of subtle truth-telling. Could be informative.

If she's that kind of friend, it's not like she's going to frost you into the next county.

 

Perhaps your biggest problem is your history. What happened before happened a long time ago. You were different then - and so was she.

 

I once (finally) fell for an old friend who was my best friend senior year of highschool. It took me 17 years to work up that head of steam. The night I finally made it obvious to her......I felt just like the leading man in a bad comedy movie. It was hysterical.

The result? She handled it like a pro.....and like the good friend she was (and still is.)

 

Bottom line: You don't want to lose this friendship. Nor should you have to.

You'll be alright. Your instincts are good. Trust in that friendship. You guys obviously care a lot about each other. And that makes it special and unique.

Good luck to both of you.