I [35M] would like to start dating but I can't tell the difference between friendliness and interest. I've been told that seeing everyday-type interactions with women as possible dating opportunities makes me a creep. Given my social difficulties, how do I find a balance?

Just like it says in the title.

-I mistake friendliness from women as interest WAY too much
-If I'm feeling attracted to a woman, and she's engaged me in deeper-than-just-small-talk conversation on a few occasions, and if she's single, I start getting my hopes up, and many times will eventually ask her out
-I've been rejected dozens of times due to this. (I can take those rejections in stride and gracefully make an exit)

I've asked for advice in a different corner of the internet and was told that my looking at mundane interactions with women and asking myself...could I be interested in her?...could she be interested in me?...am I seeing enough here over a period of time to take my chance?...makes me a creep. "Always on the prowl," were the exact words used.

I don't want to make women uncomfortable, but I don't want to be alone forever either. How do I find a non-creepy balance between "Today you could meet someone who is interested in you" and "Wait until a woman makes her interest obvious before getting interested in her" (and no woman has ever been obviously interested in me)?

/TLDR

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More information if you're a glutton for long, wordy posts:

I seem to get some of the classic signs of interest...deeper-than-average conversations, good eye contact, the curiosity of my life and experiences, willingness to keep a conversation going or talk to me again on separate occasions...but those overlap with wanting to be friends as well. I've never experienced some of the more flirtatious signs of interest...eye contact/smiles/glances from across the room, physical proximity/orbiting, physical touch, suggestive banter, asking my relationship status (I'm to the age where I get asked if I have kids, but not whether or not I'm in a relationship). (Actually a girl did once use a lot of physical touch on me...rubbing my leg with her foot, straightening my tie, touching my arm when she spoke to me...but those signals were false-positives, she wasn't interested in going out when I asked her). On the flipside I'm very sensitive to signs of disinterest...if someone is looking at their watch, looking around, returning short one/two word answers, I know to wrap it up and move along.

I would like to be in a relationship, but even more than that I don't want to make any woman uncomfortable, so I'm shaken that my behavior makes me a creep. For 10+ years I didn't try at all with women for that very reason...I was convinced that no one was interested in me, so I didn't want to bother anyone by asking them out. Maybe I should be waiting for some of the more intense signs of interest, but I've been waiting for them all my life, and I've read that many women are shy or reserved and don't do them even if they are interested...I keep hoping maybe I've come across a woman like that, but no, evidently not.

More about me:

-Low natural social ability. I've worked hard to overcome this; I can now usually function socially adequately in most situations. Sometimes I get stumped on what to say next, but I err on the side of leaving a conversation early rather than wearing out my welcome.
-Very low romantic intuition and experience. It takes all the courage and self-confidence I have to ask a woman out, which is probably a key factor in my failure
-I am intensely anxious about how I come off to women and whether or not they have ever been/will ever be interested in me. With the number of times I've struck out, I'm afraid that relationships are just something I'm never going To Get.
-I'm a natural introvert...I try to buck that and "get out there" as they say, but some weekends I just need to be alone and recharge
-For the last two years I've tried to take every piece of self-improvement/dating advice I could. I've lost weight, worked on my social skills, improved my physique/wardrobe/hairstyle, traveled and developed new hobbies, gotten counseling, gotten out and tried to actively meet and talk to and develop relationships with people (all kinds of people, not just women). I've tried to be proactive about being the person I want to be. Mostly I've been successful
-What's socially or romantically obvious to others is not obvious to me. I've been told things like "If she's interested, she'll make it obvious." I've never seen anyone making it obvious; ergo, either no one's ever been interested, or I miss the obvious, or some women aren't so obvious with their interest
-However, two long-term friends (one male, the other female) I've asked for frank advice have told me that they've never seen women be interested in me either

Submitted November 17, 2019 at 07:55PM

Just like it says in the title.-I mistake friendliness from women as interest WAY too much-If I'm feeling attracted to a woman, and she's engaged me in deeper-than-just-small-talk conversation on a few occasions, and if she's single, I start getting my hopes up, and many times will eventually ask her out-I've been rejected dozens of times due to this. (I can take those rejections in stride and gracefully make an exit)I've asked for advice in a different corner of the internet and was told that my looking at mundane interactions with women and asking myself...could I be interested in her?...could she be interested in me?...am I seeing enough here over a period of time to take my chance?...makes me a creep. "Always on the prowl," were the exact words used.I don't want to make women uncomfortable, but I don't want to be alone forever either. How do I find a non-creepy balance between "Today you could meet someone who is interested in you" and "Wait until a woman makes her interest obvious before getting interested in her" (and no woman has ever been obviously interested in me)?/TLDR​​​​More information if you're a glutton for long, wordy posts:I seem to get some of the classic signs of interest...deeper-than-average conversations, good eye contact, the curiosity of my life and experiences, willingness to keep a conversation going or talk to me again on separate occasions...but those overlap with wanting to be friends as well. I've never experienced some of the more flirtatious signs of interest...eye contact/smiles/glances from across the room, physical proximity/orbiting, physical touch, suggestive banter, asking my relationship status (I'm to the age where I get asked if I have kids, but not whether or not I'm in a relationship). (Actually a girl did once use a lot of physical touch on me...rubbing my leg with her foot, straightening my tie, touching my arm when she spoke to me...but those signals were false-positives, she wasn't interested in going out when I asked her). On the flipside I'm very sensitive to signs of disinterest...if someone is looking at their watch, looking around, returning short one/two word answers, I know to wrap it up and move along.I would like to be in a relationship, but even more than that I don't want to make any woman uncomfortable, so I'm shaken that my behavior makes me a creep. For 10+ years I didn't try at all with women for that very reason...I was convinced that no one was interested in me, so I didn't want to bother anyone by asking them out. Maybe I should be waiting for some of the more intense signs of interest, but I've been waiting for them all my life, and I've read that many women are shy or reserved and don't do them even if they are interested...I keep hoping maybe I've come across a woman like that, but no, evidently not.More about me:-Low natural social ability. I've worked hard to overcome this; I can now usually function socially adequately in most situations. Sometimes I get stumped on what to say next, but I err on the side of leaving a conversation early rather than wearing out my welcome.-Very low romantic intuition and experience. It takes all the courage and self-confidence I have to ask a woman out, which is probably a key factor in my failure-I am intensely anxious about how I come off to women and whether or not they have ever been/will ever be interested in me. With the number of times I've struck out, I'm afraid that relationships are just something I'm never going To Get.-I'm a natural introvert...I try to buck that and "get out there" as they say, but some weekends I just need to be alone and recharge-For the last two years I've tried to take every piece of self-improvement/dating advice I could. I've lost weight, worked on my social skills, improved my physique/wardrobe/hairstyle, traveled and developed new hobbies, gotten counseling, gotten out and tried to actively meet and talk to and develop relationships with people (all kinds of people, not just women). I've tried to be proactive about being the person I want to be. Mostly I've been successful-What's socially or romantically obvious to others is not obvious to me. I've been told things like "If she's interested, she'll make it obvious." I've never seen anyone making it obvious; ergo, either no one's ever been interested, or I miss the obvious, or some women aren't so obvious with their interest-However, two long-term friends (one male, the other female) I've asked for frank advice have told me that they've never seen women be interested in me either