Ok that's some good insight. So you can start by working on that..... the non-smiling intensity. I think your friend verbalized it well with the comment of coming across as serious and intimidating. That is definitely something you can work on. Smile more, joke more, try to get silly. Also, you mentioned that you used to have a difficult time making friends when younger. Those scars run DEEP and take a long time to heal. They really form who you become as an adult and it can take a lot of effort to undo that damage. One of the BEST ways you can break out of it is to practice social freedom exercises. This means just doing silly awkward sh*t in public that will cause strangers around you to judge you and look at you funny. It is really stepping outside of your comfort zone but doing it helps you become much more confident and care/worry much less about what other people think of you because you will realize that most people literally don't care. Most people will ignore you, maybe chuckle a little bit, maybe give you a funny look, but then they go on their way with their lives and that's it. It's not like back in school where you might say or do one stupid thing and 50 kids then tease you about it for 10 years subsequently. Examples of things to do: Walk up to a random girl on the street and ask her if she will marry you. Stand on a park bench flapping your arms like a bird with a crazed look in your eye. Do the moonwalk or dance down a sidewalk. Do jumping jacks in the middle of the sidewalk. Walk up to a random woman and tell her you have STDs. The goal here is to stop taking yourself so seriously, and to help you realize no one else takes you that seriously either. You need to develop an IDGAF attitude. It will be hard at first, and it will take time to undo those scars, but trust me it will be worth it and you will immediately start to feel better as you see how well it works.
Second thing I notice is that you sound like you are texting women a lot, and it sounds like it's not been working well. IE some women who may have been interested are losing their interest after you text them. Without seeing the texts, it's hard to say what the issue could be, but my experience is that you can't build attraction over texts, and you have to be careful with the amount you text. You should be a popular, busy guy with a lot of opportunity with women. If that doesn't describe you right now, then you need to at least pretend that is the case until it is. How do you do that? Think about a guy who is like that, and what would he do? Would he have a lot of time to text back and forth with one chick? Would he be interested in investing a ton of time texting with a girl he hasn't even slept with yet? No to both. So you text her to setup dates and that's it. You build rapport in person, not over text. If she texts you, you should respond, but only send 2-3 messages back and forth max, and then tell her, "Hey I have to run, but I'm looking forward to Friday night!" Convey that you are busy, but interested in her and looking forward to seeing her. Also, your banker woman story, it sounds like you texted her the same day (within hours) of getting her number. Again, that's not what a busy popular guy with a lot of options would do. He'd wait a couple days and then text her. And when he texted her, it would be to setup a date, not shoot the sh*t. Also, based on your banker story, it sounds like you didn't ask her out on a date, but instead just texted back and forth? Women want a guy who gets to the point quickly, and YOU should want to get to the point quickly so you can determine whether or not you are wasting your time on someone. If you don't get to the point quickly, women will think you aren't confident and that you are waiting for them to give you a sign that it's safe to ask them out. That's bad. If I got that banker's number, I'd wait 2-3 days and text her:
Me: "Hey Sarah, it's _____. Was good meeting you the other day."
Her: "Hey ____, yeah, you too"
Me: "I enjoyed talking to you the other day and would love to meet for a drink soon. How about this Friday 8pm at the Brown Cow Pub?"
If she says she is busy at that time and gives no alternate dates/times, I won't even reply to her. If she says she's busy but gives an alternate time, I'll set the date and tell her I look forward to it and then I will not initiate text again.
Another thing - sounds like you are hitting on a lot of women while they work. This is a viable strategy but in my experience, the odds of success are reduced. It can be easy to misinterpret a woman being nice vs being interested, because it's her job. And second, some women feel like it's wrong or risky to accept dates with customers... like there may be policy against it or other bad things could happen. So if you want to do day-game women who are working, you can do it, but understand the odds will be reduced.
The more details you provide, the more we can help. The girl you went on a golf date with..... what did you text about in the days after the date, who initiated the texts, and how often did you text before she ghosted?