it is only more complex if you make it that way.
i will tell you a little story to maybe give you help.
in HS, i dated this girl that i was best friends with for about 2 years prior to us dating. i never thought i would date her simply cause she was a little heavy, and you know, HS kids are very judgmental. anyways, it just hit me one day that i liked her more than a friend, and i already knew she liked me, so, i said screw what others think, and i started dating her. about 6 months later we split up cause i felt she was smothering me with cards every day saying how much she loved me and crap, and i was like yo biotch, im only like 14, i need some space. talking about marriage and ----, biotch, you crazy. so, yeah, i dumped her.
she got really bitter towards me for that over the next couple years, but, i just kept trying to keep the piece since we were such good friends before this. finally we started talking more and becoming friends again, meanwhile she was dating the guy Will. she dated him till about a year after high school.
one night, after i had recently broke up with a girlfriend, i took her some flowers for her bday, and noticed that Wills car was at her house, so, instead of knocking on the door, trying to avoid a problem, i left the flowers on her doorstep with a bday card. well, when he went to leave a few minutes later, he saw them, took them in (keep in mind he hated me) and he threw them at her and said they were going to split up and stormed out. she called me crying. so, i immediately went over to comfort her.
she told me what happened, but, would not give me permission to f*ck him up, so, i just stayed there with her. i then told her that i still had feelings for her and started kissing her. next thing i knew we where hitting skins and Will became an immediate thing of the past. to make it a little better, it was the first time we had ever had sex since when we dated in HS, we were still young and only kissed. so, it just made the get back together that much sweeter, especially when Will tried to crawl back and she denied his a$s. lol
so, dude, do what your heart tells you, stop thinking about it so much. just kiss her.