How do I approach a guy who says he's "boring irl"?

thats the thing
if, say, i was the guy in question, and suspected you of liking me, id rather push you away and get nothing, than have my life fucked up, because you eventually change your mind
that's just how some of us are
either he got burned in the past, or never associated with the whole concept of the relationship, you cant fix it
move on

You approach him from behind and jump on his back. Then you can ask him out, pinch his cheeks and mime 'yes' with his mouth.

Maybe whatever girl was with you left you because you were a dick

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maybe she latched onto me without actually knowing me
maybe she realized there are options in life for me, but not for her
maybe she told me she cheated on me due to feeling of guilt, and I left her
who knows

Nice projections, incel KEK

thanks

Can you give some more details on yourself and the guy?
How do you know him, how old are you guys etc.

if he's not boring on text, that probably means he isnt boring but just really repressed. you could probably help to bring him out of his shell. be not boring around him so he's got a vibe to work with. and make sure he knows that you like him and why. this will make him realize that it's ok to be himself

I'm gonna put my dick in your butt.

Ask him on date. Park and burger.

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Is this why girls don't not take initiative? Are they scared to fuck up?

There's a number of reasons. For me personally, yeah this would be part of it.

I don't think shy people in general want to take the initiative, but because it isn't expected of women I take "advantage" of that and don't try.

Granted, it's pretty plausible that I've lost connections this way, but I'm a socially awkward mess, so I'm doubting it was too many.

You miss the 100% of chances you don't take. For all you know, the person you like could be as shy in regards to asking someone out.
Don't be afraid of rejection, since the worst thing that can happen is you stay where you are now.

I mean, I get that, but I worry I'll look a bit like a creepy girl. A lot of the guys I start feeling attracted to are my personal friends, and I don't want to risk being the one to ruin the friendship with unrequited feelings.

Assume his past experience says that what he is interested in, other people (girls) aren't.
Ask what he is interested in, tell him your interests .. either you will share interests or not.

You like him based on what?

Good luck making him open up before you lose interest.

So you expect them to ruin it? Fuck sakes, man up... yes I know, point still stands tho.

Creepy is what I would not describe a woman, who is taking initiative.

I'll keep it in mind. I just don't think anyone who is as awkward as me wants to take the initiative. I guess I could ask some guy I've been thinking about a bit for some coffee when I see him tomorrow.

We're at school together, and he's in one of my classes. We started talking through Instagram because I guess he found my account. Other than that, we haven't spoken before in person, but I texted him yesterday saying I wanted to talk to him in class.

He's funny and we have very similar humour that I don't really share with anyone else I know. It's not really about his appearance to me, but I don't think he's unattractive. Our conversations are really interesting and I actually enjoy talking to him. I just hope his shyness doesn't impact me having a relationship with him.

It just means he has no aspirations and/or ambition. If that’s your thing, then it’s all good.

In pic related, the "creepy" version is just cute (and frankly I'd be much more suspicious of the 'suave' one).
You're not a fucking threat, there's no way you can come off as creepy to a guy unless you actively try to, on the order of saying "I sacrifice puppies to the shrine of our future undying love".
Just approach him.

This is true

Give him a hand job.

I tell you hwat - you go ahead and tell him "men" from the internet promised you that he would go out on a date. He can't refuse now. All objections straight to Jow Forums.

Top. Men.

Eh that's not always true. If someone is completely repulsive then they'll come off as creepy.

Keep in mind that I'm not talking about a "Waahhh I don't have a thigh gap!" sort of thing, I'm referring to like "I don't really want to be close enough to talk to you until you've taken a few showers..." kind of repulsive.

>not taking a shower before asking out your crush

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Nobody wants to take initiative, everyone would LOVE if shit just fell into your lap
The reason people take initiative is because they want results. In my opinion, if none of these guys make you wanna ask them out, maybe you're just infatuated.

>If someone is completely repulsive then they'll come off as creepy.
"Someone"--if it's a guy, yeah, because they are much more threatening to a woman than a woman is to a man. If you were approached by someone gross, you'd find it gross, but not creepy. And the approach wouldn't be what makes them gross, whereas a potentially threatening male approaching is putting himself in a position to be labeled creepy.