You sound a lot like myself, so I’m going to offer a ton of unsolicited advice you are welcome to ignore. This is how I went from occasional dates to strings of dates within a few months. It does take a bit to get going. It has worked for me and worked for my friends (those who actually did it), so I think it can work for most anyone.
Meeting single women became so much easier (for me) when I learned one technique: find something you enjoy doing that will bring you into contact with the type of women you’d like to meet, but only do it simply to do it, for the joy of it. Never try to “just meet women” while you’re doing it. Not even once in awhile. No pulling birds Thursdays. Women aren’t stupid, they’ll know what you’re up to and they talk. So don’t meet women: meet everyone. Want to meet more women? Do more of the activity and meet more everyone there too. Basically, forget about meeting women, just do the activity and meet people through that.
Be nice, be fun, don’t be afraid to be vulnerable, and aggressively be yourself. Be yourself so hard, do NOT fake anything. Dress nicely, smell good, and don’t be afraid to stand out. For example, I’m a little bald guy and am a snappy dresser with my own style; love cats, hokey horror and sci-fi movies, and baking for people; and have a deep voice. I took voice lessons so I could sound more like I want to, share my love of my fur children with fellow cat people and my taste in movies with fellow movie people, and I bring baked goods to events. In short, I let who I am shine and people who like that remember me and like me for it.
If you meet a woman and it appears you two have chemistry, be really up front and do one thing soon: pull them aside and ask them if they’re into you or if you’re reading the situation wrong. You have three likely outcomes: they’re into you, they only want to be friends, or (least likely) they’re immature and talking directly about feelings scares them. No matter what, it’s a win: potential girlfriend, potential friend, or you’ve weeded out someone immature who you probably shouldn’t date or be friends with anyhow. Again, just do it early so you don’t get your hopes up and you get crushed if there’s no interest. You know what’s really impressive to many women? Someone clearly and respectfully asking how they feel and handling the answer with grace and compassion.
That’s it. This approach has so many advantages. You do something you enjoy and you do it often, so you get good at it. This makes you more interesting. People love interesting people.
By aggressively being yourself, friends and love interests want to be around you for you and want more of what makes you, you. No lies and stories to keep up, which is exhausting and will ultimately fail anyhow. Lie if you want to get laid and are an absolute piece of shit. Be genuine if you want to form lasting connections.
You expand your social circle, which helps with meeting more people. Assuming you’re a nice person, people will want you to meet their single friends. It just happens, especially through female friends. That hypothetical woman who turned out not to be into you? Show her you’re someone who listens to and respects women and she’s more likely to think of you when her friend is grousing about being single and lonely.
Success Stories
I met the vast majority of my dates and girlfriends through friends this way. One ex I met after our mutual friend (who I had just hooked up with and it immediately turned out we had awful, AWFUL chemistry) introduced her to me because she knew I was a nice guy and thought we’d hit it off. This was the week after we went out. All based on an okay date and the worst sex in both of our lives - I know, we both talked about it later.
I met my wife through a woman I was initially interested in but she was SO not into me. We ended up good friends. I later met her friend and was instantly into her, hard. She was also interested but very guarded, but she dropped that guard after my friend spoke well of me and how I treat women.
That’s really about all there is to it. If you have questions, I’m an open book.