Always having to be the first to say hi

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Typed up several huge paragraphs but the stupid new captcha "I'm not a robot' feature deleted everything. Sigh.

Long story short, I always have to be the one to message old friends and acquaintances. Don't talk to my old high school friends anymore because they don't bother to message me. Never got invited places in high school, wasn't popular in the slightest since I had severe anxiety.

My counselors have suggested that I 'go out for coffee with a friend' - and yet I only used to do this in high school by asking in person. I didn't get a cell phone until university. Don't even use the cell phone anymore, had some people's numbers but they just stopped texting eventually and forgot that I existed. I also have dysthymia, persistent mild depression, and don't smile very much because of this. It's something I can't help.

Problems with retaining friendships always seem to revolve around the issue of people eventually losing interest in communicating with me. I did have people to talk to in clubs at university, but these girls were too 'cute quirky' and tumblr-esque, and they all seemed to have their own clique already or a best friend who was always hanging on their shoulders. I'm not good in cliques, never had my own 'group' ... usually just one best friend. Is that unusual?

How do people gain new 'meaningful' friendships when old ones expire? (Would help to get answers from people who have had similar social struggles as I have).

I'm going through the same thing and it takes a lot more effort. People have lost interest in me and its humiliating going back having to contact them just so I have some sort of social interaction. I try to avoid contacting people who never ask how I'm doing unless I feel desperate

The best thing I think is to talk to people and make more of an effort to put myself out there, exhange emails or numbers with someone I can get along with. It is awkward and unnatural at first but does get easier after a couple times. Also trying to look for groups who share my same interests. Not because I want to fit in but to help me with my loneliness. I will always be different but even though I have aspergers I am still human and I need other people.