How can I chase after him?

[katestar]

How to win his heart?

[CalmMind]

You're 32 not 17. It's really not that hard. You use your talker to tell him how you feel lol. If he's interested, congrats you guys will get to explore that and I genuinely hope it works out for you two. If he's not take the L and enjoy your life. I would say at least half of this website can be boiled down to just talk to the other person, don't over think it, and be honest.

[katestar]

We've been friends since we were teenagers.

[CalmMind]

I stand by my comment. How do you know he hasn't been crushing on you this whole time?

[katestar]

Good point. When we were growing up. He was thinking about
It

[CalmMind]

Probably still is. Just shoot your shot. That said, I don't know you and I don't want to ascribe motives to you so just take this with a grain of salt: If he thinks you're approaching because you've gone through your "loose days" and are ready to settle down he's likely going to think a few things:
1. You've been keeping him in reserve as a "nice guy".
2. You're settling (not the same as settling down) for him, i. e. last option.

We (men) think this by and large because it happens so often to many of us. Hasn't happened to me but I've seen it plain as day in a lot of my friends.

[katestar]

Go on

[CalmMind]

What do you mean go on? I've said my piece.

[katestar]

Let me guess. My guy friend doesn't want to settle down?

[CalmMind]

I didn't say that. I said if you've lived your life how I described then he'll probably not be interested if he has any self-respect or you'll have some serious conversation needed before he's willing to commit. I wasn't commenting on his willingness to settle down in general I was commenting on how he perceives your approach based on the relationship you two already have and how he views your past.

[katestar]

If he doesn't have any feelings for me.

[katestar]

He doesn't know that he will understand that I am really attractive.

[CalmMind]

Let me put it another way. Let's say you and I were friends. Our whole friendship you've seen me out whoring around with any woman that will put out. Through all of this we've maintained a really good friendship but obviously I haven't approached you for anything beyond friendship. Then one day I approach you and ask if you want to start dating, despite me having a history of failed relationships and casual encounters with no commitment. That's what men are seeing when a woman approaches with THAT past. It's not really a gendered issue as such, it's a lifestyle issue. Hope that helps clarify.

[katestar]

My guy friend is single.

[CalmMind]

Okay. If he's single, then go for it. If he says no it doesn't really matter what his motives are, he said no.

[katestar]

He will say yes.

[Avicenna]

Just ask him out

[katestar]

Ask out my guy friend?

[Avicenna]

If you want to date him, yes

[katestar]

He's a single man. And he has been my guy friend for 24 years

[Avicenna]

Well then why do you ask how you can chase him? You know him well enough to ask him out. Or not. It's not rocket science.

[katestar]

What?

[Avicenna]

Who is "him" in your question? The guy you want to chase?

[katestar]

My guy friend.

[Avicenna]

You don't need to chase a guy you know that well- all you have to do is ask him out.

[katestar]

Like on a date?

[Avicenna]

If you want, sure, but since you know him so well, if you want to be his girlfriend, all you have to do is ask him to be your boyfriend. It's really that simple.

[katestar]

Good. But I need a plan.

[Avicenna]

Why do you think that?

[katestar]

To get his attention. He acted like a jerk. He's a actor.

[Avicenna]

he's your friend- you automatically get his attention

[katestar]

I've known him for 24 years. He doesn't know what he is missing.

[Avicenna]

OK, this is the last thing I'm going to say- stop wasting your time on here and ask him out.

[katestar]

If I get his attention.

[katestar]

Maybe I should wear a attractive outfit.

[Avicenna]

You can do that, but it isn't necessary since he'll obviously pay attention to his friend of 24 years!

Thanks for the MHO

[Idkwtfimdoing96]

You shouldn't chase anything or anyone. If it's meant to be yours it will, trust me. Just be patient

[EmmaMary]

Don't fuck around just straight up tell him your feelings... Simples.

[katestar]

Well. Anyway. You make a good point about it

[EmmaMary]

It's the only way to be... Good luck. x

[EmmaMary]

Thank you so much @katestar for the MHGirl. x

[Gent207-2]

You are Absolutely crazy for this guy lol

Your last dozen posts have all been about him and how to win him over. But in the end you are just too scared to do anything

[katestar]

I'm sorry about that. I won't do it again. I'll stop asking questions

[Gent207-2]

@katestar
I'm not complaining I am stating an observation.

Your response however suggests that you are super sensitive to any form of rejection possibly due to your upbringing?

[katestar]

You're right about that. I'm done with asking questions.

[Gent207-2]

@katestar
Well I'm not, why are you shutting down?

[katestar]

Because I'm done with asking my questions about my feelings.

[Gent207-2]

@katestar
I'm not done asking or discussing your feelings or thoughts on this matter

[katestar]

Oh. Really?

[Gent207-2]

Yes!
So I am curious what do you look like? And what does he look like?
Pic please

[katestar]

How?

[Gent207-2]

@katestar
We could take take this to messages or you could write out a description?

[dustybiker]

Just be bold and ask. Sounds like you’ll regret it if you don’t.

[Danny_dan92]

If he doesn’t show interest then he isn’t interested