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Socially inept 20-something wondering if I should ask my friend to go out with me.

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First, a little about me.. I'm a guy in my late 20s and recently got diagnosed with (severe) asperger's syndrome. I haven't really learned to handle it properly yet and for those that don't know, in this context, it pretty much means that I'm terrible at expressing my emotions, interpreting the emotions of others and picking up on signals. I'm not sure how relevant that is, but I tend not to 'make a move' unless a girl has made it explicitly clear that she is interested in me, otherwise I simply do not know... and I'm sure you all know that girls spelling out their feelings plainly towards a guy they like is not entirely common.

The reason I'm posting here is that I've been talking to a female friend regularly for quite a while and I've developed stronger feelings for her. It isn't love at this stage, but I could see it turning into that quite easily. I don't want to ruin my relationship with her as a friend and I'd gladly remain in the friend zone and let the feelings that I have now subside, if the alternative is to scare her off and lose her as a friend.

I've known her since I was a child but we'd had very little contact for a long time and, since around a year ago, we have been speaking most days. Sometimes she seems really into me, though other times I feel like I'm far from a priority for her. What makes it more difficult to interpret is that we live on opposite sides of the country (although I will be moving nearer to her for unrelated reasons in the next few months), so we only really talk on the phone or through text. If it's a phone call then generally she is the one who calls me (she has a much busier life than I do so I tend to let her take the initiative when she's got time) and if our texts die down then she will send me a silly message or a funny video or something without motive or purpose to get my attention again, usually within a day.. although this could just be her innocently relying on a friend to alleviate her boredom. On rare occasions we video chat and it feels like there's a lot of chemistry.. lots of giggling and not-so-awkward silences as we just smile and look at each other... but being so physically removed it could just be my imagination.

I know it's never black and white (despite what my neurological condition would lead me to believe), so if there's no clear cut 'yes she is into you' or 'you're already well in the friend zone', or some other obvious thing which hasn't occurred to me, then I guess I'd just like some advice on communicating my feelings without damaging our friendship.

I guess anyone giving a solid opinion on how she feels might need more detail on how we interact, but I'm going to stop this essay here and if anyone wants more specifics then I'll add them in a reply.


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It never hurts to ask. Just ask her confidently and with no pressure. It should be easier the more you do it. I don’t even worry at all asking a woman out anymore. Granted that’s after enough times and plenty of rejection. You said you are plenty fine with remaining just friends so really should be no pressure. Good luck man go get her.

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Women seek men with resources, eg spend time, good listener, protection from unwanted male attention, and financial.

Know that as her friend, she already has access to your resources. So you really have nothing more to offer here. Telling her how you feel will not change her access to your resources. 

Women want men that will lead in certain areas and share all their resources. Women are competitive too. Women typically vet their men before getting into relationships too. Use this knowledge to your advantage.  

Know also that at your age, your resources are inherently limited. A man’s resources increase over time. Your competition is older, more resourceful men.

Best advice: be excellent in what you do, especially resourceful, be desire-less, and be scarce. Only then do you have a good chance. 

No matter what, focus on yourself. Focus on becoming a resourceful, young man and women will be attracted to you. It takes time to become that person. 

Best of luck!

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How near to her are you talking? Why are you moving? If you're moving closer to her in only 60 days, I'd wait and gauge how things are going in person. Make sure you set up your new life there by making new friends and engaging in hobbies. You never want to make one person the sole center of your social life or that will be smothering to them. In my opinion, you're kind of caught in a tough spot. Because if you ask her out and she says no but you remain friends, a new woman in your life might ask about the close friendship and have the question, "Were you ever interested in her romantically?" And if the friend's new bf sees you have a crush on her, he won't like your presence in her life.

When male/female friendships aren't totally platonic, they often have a short shelf life for obvious reasons.

I always say take a risk rather than not. Of course if you can read the signals properly, it's a big help. Never divulge intense feelings. Simply say, "We get along so well. What would you think of giving dating a try?"

If the answer is no, it might be awkward for a while, but it will usually blow over. And always remember it's normal for friendships to evolve. Some grow, some get placed on the back burner, and some end. Make sure you always have at least a handful of friends or activity/hobby partners, so that if one friendship ends, you still have a support system of other friends. Good luck and let us know how it goes.

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 Don't have to make this complicated, just say you are interested in her and want to take her out on a date. That's how it's done. No one on this planet knows what she is thinking or what she thinks of you. The only way to find out is to ask her for a date...then her answer will give you your answer. No need to express feelings at all.

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Thanks for the advice everyone. Feeling much more relaxed about the idea after reading all this.

I think I'll listen to Andrina and wait until we are able to meet in person.. and then if things feel right I'll just say we should go on a date or something.

On 1/23/2021 at 2:58 PM, Andrina said:

How near to her are you talking? Why are you moving?

We would be in different cities, but within a 20-30 minute drive of each other.

I'm moving back to the area I grew up in, mainly because I don't know many people where I'm living now and I've recently gotten back in touch with some of my family... so I'm building that support network you mentioned.

Using my partner as a crutch has been an issue in the past, though I didn't recognise it at the time. *Hopefully* I've made enough changes that it won't be an issue.

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