A lot of guys really don't understand women. I think it's a mistake to look at them as equals when you're trying to win someone over. In terms of social power and influence, women are almost always vastly superior to men. Any decently hot woman spends a huge amount of energy turning down guys, beating them off with a stick, and trying to be selective to weed out poor prospects. Some women are shy and have trouble dating, and I'm generalizing of course. Most normal good looking women have power in social situations and have probably done more socially than you.
Now, this doesn't mean putting them on a pedestal and trying to kiss their feet and beg. That's going to come across as pathetic and weak, and men are already weaker than women when dating starts.
It means you really have to be a formidable person who is better than most other guys. You have to be able to look a smoking hot girl directly in the eyes and not look away. You have to be confident. You have to have enough of a presence financially, physically, socially to be interesting to someone that experiences life on a different social level than you. When you have or project that kind of strength and confidence, people find you interesting.
If women can buy into the fact that you're their social equal or superior, then they find you interesting and mysterious. Women are so frequently drawn to that, that you can spend years single with no one showing any interest. But the second you get a girlfriend, other girls will be interested in you as well, and you have to turn them down. Women are looking to weed people out, like a teacher trying to flunk students and only take the top few. If they see another woman on you, they at least are slightly interested at that point.
I feel bad for guys lacking self-confidence though, or experience. That was definitely me for a long time. You need to be confident, but how are you supposed to be confident if you've hardly been with anyone? It's the catch-22 of dating. You either have to will yourself past that point in your life, or run into a nice girl that looks at things differently or who sees something attractive about you.
Even with this advice, it's still hard for me to meet people. Until I crossed that line and got some self-confidence, I had no chance. I even looked back at multiple times girls were trying to flirt with me and I was so clueless I didn't even know.
And also, even in your 30s you can meet some great women. A lot of men don't even really get their shit together until then. I was definitely a late bloomer and didn't really solidify a career until later. Once I did, got a nicer car, got a nicer place, got nicer clothes, felt better about myself, I actually met lots of women.
And by the way, you shouldn't really care that much if a woman is on "round 2." Re-read what I said at the start of my post about them beating off men with a stick and living a different life than you. Any attractive woman that is interested in men is going to be on round 8 at least. You're not the same as they are.