I’m a 45 year old male. So… my buddy Rick was dating this girl named Baylie. At the end of their relationship, things got really bad. Like Rick almost being arrested, her almost losing her two girls, they almost lost their house… ** just went ridiculous. They finally ended things as cleanly as possible, and Rick moved 10+ hours away, while Baylie stayed in the area.
Now I was friends with Baylie, before I was every friends with Rick. Baylie and I went to high school together, and I never met Rick until we both served in the armed forces together. I started inviting him to parties, and such and that’s where he met Baylie. He basically begged me to hook him up with her. By this point she was divorced and had two daughters of her own. I explained to Rick, that her kids would always come first, and that she just went through a really ** divorce, he told me that’s fine and ended up started dating her that night.
Well here’s my issue. Baylie is 5’8” tall, 145 lbs (90lbs of that is in her bra), long wavy blonde hair, big baby blue eyes, an amazing smile, and an ** that you just wanna bury either your tongue or ** in depending on what you’re into. Needless to say she’s phenomenally gorgeous and awesome to hangout with also. I have loved her since high school, and now that ricks gone, and she’s single I kind of want to throw my hat into the ring.
I know she’s been screwed over by a lot of guys, I also know she has her issues, but don’t we all. My question is, would I be over stepping my bounds between me and Rick, trying to date her or sleep with her? I feel like I’ve waited long enoug, and I’m not getting any younger. I truly feel like Ted from HIMYM, thinking she could be the “One”. Any advice would be truly appreciated!