@SnowblindNYR a few more pieces of information.
-For the Morocco story, my best friend who does pretty well with ladies gave me some of the best advice when I was dating a girl in my early-20s who would get angry at me for anything and everything: "look you gotta be yourself. At the end of the day you're a decent human being with a big heart and if some chick can't see that and is going to be appalled by some one-liner or joke, how the $^## are they gonna do 10 years into a marriage?"
-The "not ambitious" thing: look up hypergamy. New York/Miami/Los Angeles are the three most exponentially hypergamous cities in the US. It's nothing with you, she just may want someone who is making 250K per year. There's also social hypergamy. About 7-8 years ago my friend tried to set me up with this lawyer. Pretty girl and I knew she wasn't marriage material (I didn't feel it with her on interactions other than a physical attraction). She wouldn't go on a date with me because I wasn't part of that elite NYC professionals scene, was "only then working on an advanced degree," and as everyone on this board knows, I'm never going to wear dress shoes or tuck my shirt in on weekends when I'm just lounging. I'm in band or Rangers t-shirts/shorts/baseball caps most of the time when I'm not working or at a formal event. She wanted me to be in a suit and tie at all times and do the whole socialite dinner party nonsense. Nope.
-As for conversations, I'm sure you are 100% a great conversationalist. I am too. There's this certain type of charm or "messing" you may have to improve on. I've never met you so I can't say. And I'm not trying to offend you. As with all my posts on this board I am coming with the mindset of what the teacher told Holden in "Catcher In The Rye" or the Star Trek mentality which is write down your journeys and experiences and share them with other people so you can help them in their journey and live better lives. If you or anyone on this board thinks I'm full of bologna/salami/prosciutto that's ok. You can ignore it.
I was very shy and had low self esteem at various points in my life. I've learned that I'm on par or better at conversing than 90% of the people out there. I'm sure you are too. Remember, everyone has problems that they hide. You're probably smarter than most.
A lot of time my friends who do best with women know how to tease them or play with them. It's not so straightforward. They make them laugh and also put them down a little. Not in a bad way, but playful way. Women want to feel.
You will improve with flirting and playfulness. Read books on it and practice.
The last thing is about drama. Women are more emotional creatures. My ex from my mid-20s who I am still very good friends with (she texted me today messing with me about my stomach, saying I'm an old lightweight and don't drink wine anymore lol) once told me that she didn't enjoy or handle things well when everyone was getting along, she needed a little gossip or spice, and even today a coworker via Skype said "what's a day without a little good drama?" and I hah hah'd but then in my mind referred back to the beginning of this paragraph.