Back Story: I have known this girl since about 7th grade and have been crushing on her since I was a freshman. We went to homecoming with her but due to my lack of experience with girls I did not handle it right when I wanted to take things a bit more seriously. Basically I was way to immature to be in a relationship (didn't help that I was 4'9" with a face that looked like it had just been molested by mosquitoes). Fast forward to junior year I had another chance to be with but fucked it up royally, AGAIN. After we graduated I went off and joined the USN and she went to college. She and I kept in contact for pretty much all my four years of my enlistment. During that time she had met someone else, lets call him "Jackass". She has been on and off with Jackass now for about two and a half years; not a very stable relationship looking from the outside in and all of her friends agree with me, she just cant seem to drop him.

I have been running situations through my mind trying to think of the best way to tell her how I feel. So my question is this: Should I tell her while she is still with Jackass or wait till things go south with them. If she is truly happy with Jackass, I don't want to tell her how I feel while she is still him and ruin our friendship, possibly breaking them up in the process (home-wrecking is not my forte). If I wait too long I fear I will placed in the dreaded friend zone. Neither option sounds very appealing to me. Hopefully you guys/gals can help me find another path to success that doesn't require burning some bridges.
user
Crush on
assistant
Back Story: I have known this girl since about 7th grade and have been crushing on her since I was a freshman. We went to homecoming with her but due to my lack of experience with girls I did not handle it right when I wanted to take things a bit more seriously. Basically I was way to immature to be in a relationship (didn't help that I was 4'9" with a face that looked like it had just been molested by mosquitoes). Fast forward to junior year I had another chance to be with but fucked it up royally, AGAIN. After we graduated I went off and joined the USN and she went to college. She and I kept in contact for pretty much all my four years of my enlistment. During that time she had met someone else, lets call him "Jackass". She has been on and off with Jackass now for about two and a half years; not a very stable relationship looking from the outside in and all of her friends agree with me, she just cant seem to drop him.

I have been running situations through my mind trying to think of the best way to tell her how I feel. So my question is this: Should I tell her while she is still with Jackass or wait till things go south with them. If she is truly happy with Jackass, I don't want to tell her how I feel while she is still him and ruin our friendship, possibly breaking them up in the process (home-wrecking is not my forte). If I wait too long I fear I will placed in the dreaded friend zone. Neither option sounds very appealing to me. Hopefully you guys/gals can help me find another path to success that doesn't require burning some bridges.
user
Crush on
assistant