Relationship Advice? IF YOU GUYS HAVE A BF CAN YOU PRETTY PLEASE GET ADVICE FROM HIM TOO

THIS IS REALLY REALLY LONG AND IM SORRY.

Any advice would be great, but from a guy and a girl would be great!

I seem to have a lot of trouble with crushes and was wondering if I could have some advice.

Unfortunately for me, the last four crushes I've had have all ended up liking and/or dating one of my friends. Most of them have been apologetic and I've encouraged them to do it, because who am I to stop someone from being happy?

So there is this one guy, let's say his name is Hayden, who I have on and off liked for a while. He dated my best friend, but to be fair I liked him before anyone else did and she's absolutely 100% okay with me liking him and ships us every second she can get.

I didn't like this guy for about two months, I was content with just being myself. But that changed when I started walking home with him. I was completely expecting silence and awkward questions but the conversation flowed naturally and I had a great time.

Everything was going great until I found out he STILL liked one of my closest friends. Despite being my close friend, she very much lead him on for a solid six months and then when she finally said yes, they lasted a whole three days in which they didn't see each other.

He sent her a long ass paragraph about how he's "fallen" for her and how although he's faced rejection multiple times he still wants to try. She sent this to me as to not start a fight, worrying about if I found out some other way and got offended she hadn't told me.

Now here comes my problem. I really like Hayden, and I just want him to be happy. Normally I'd just say if she makes him happy then so it be, but this girl tells me everything. She's head over heels for another guy and I don't think that will be changing anytime soon.

I'm struggling to decide on whether to ask him out, beg to give me a chance, tell him she's going for another guy, just leave it?

My concerns are:

I just want him to be happy, but how can he be happy pining over a girl who doesn't like him back?

If I were to ask him out and he says no, would I really wanna give up the walking home?

If I were to tell him she likes someone else, would that make him more unhappy?

If I just leave it, am I going to end up miserable?

I would love advice from both genders, and thank you so much for taking the time to read my long ass paragraph.

🙊