Saying Awkward Things

I’ve been introspecting lately, and I’ve noticed that a recurring theme in my life is that, for a quiet person, I’ve said a lot of socially unacceptable things throughout my life, even when I was little. I’ve alienated more than one or two friends for life with some strange things I’ve said. On a possibly related note, I’ve never had a girlfriend before and, since I was little, have had some really odd ways of expressing my attraction. So there has to be some kind of diagnosis for all this, right?

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hartfire

Worth getting tested by a shrink. Maybe you might be a bit Aspergic (higher end of A.S.), or perhaps impulsive which can be one of the 18 traits of ADHD (no correlation with IQ). If the diagnosis is positive, you can get help to improve your social skills.
If it's negative, you can still get help by reading about and/or doing courses in Non-Violent Communication (NVC). You can look it up on line and watch Marshall Rosenberg demonstrating on YouTube. You can also find or create a free weekly practice group. NVC is about learning how to listen with empathy, how to hear and recognise the emotional tone and needs in what people are saying. Recognising their need makes it far easier to respond in ways that they welcome.
A good way to initiate conversation is to ask about people's interests, passions or latest concerns, and then draw them out about those topics. It involves being curious and genuinely wanting to get to know people. If they reciprocate by showing an equal interest in you (ie, asking similar questions of you) then you may have the beginnings of a possible friendship.
As for expressing attraction, it's better to wait and develop rapport first. If that develops, then try the open and honest approach, "I feel attracted to you." That gives her the opportunity to say whether she feels the same or not. If it's a no, be prepared to accept a no graciously, ie, the friendship doesn't end; it just doesn't progress and leaves you free to create and explore other friendships.
If you [i]do[/i] have a neurological condition, you might find that a woman with the same issue would makes a more compatible partner.