I've discovered several threads on the issue, but none that really got in depth or answered my question.

Here's the situation...I've recently gotten involved with a younger, inexperienced chick (I'm 28, she's 18). Long story short, she's crazy about me, and although I really don't like to get seriously involved with girls under 25, I'm actually pretty crazy about her too. (I've found that dating younger, inexperienced girls can lead to some of the most loyal, lifelong friendships/hookups/girlfriends, but thats a different topic).

Anyways, the deeper this girl falls for me, the most insecure she gets. Although she hardly will admit it, I can tell the issue is that she thinks that she's not good enough for me and that I'm going to find an older, wiser girl to be with. Her insecurities are really getting annoying though. Sure, I can just ditch her and find someone more on my level, but I'm not going to. This girl is someone I want in my life, and as I do for all people in my life, I like to help them improve.

I'm an evil good guy though. A realist if you will. Now here's the thing...her insecurity is like an invisible leash for me. Honestly, I like every girl I'm with to feel like I might be slightly out of their league, and it just fits my style of living well. Some guys work well as assholes, some are great at being nice guys, I'm a little bit of both based on the occassion. As someone who is very sensitive to a girl's level of attraction though, I can tell that overloading her with confidence will be detrimental, and that she psychologically needs a guy that will make her feel a little bit insecure (again, something she'll never directly admit to).

I guess my question isn't really specific, this is just a discussion on managing security levels. What good or bad experiences have you guys had building a girl's self esteem? Which psychological methods do you find work well, or terrible, especially from a perspective of seduction and attraction. I'm sure there are many ways to build a girl's confidence that will also make her unattracted to you. Is there a holy grail of seductive confidence building? Is it even worth being involved with an insecure girl? I'm interested in hearing your perspectives, and also sharing my experiences with this girl. Thanks for reading!

Let me contribute what I have done so far, how it worked, and what I plan on doing in the future (this is the first insecure chick I've decided to stay with so I have to use her as a primary source of examples):

1. Reinforcement: I think I saw someone around here call this shaping? Either way, its an old psychological tactic where you reinforce someone's behavior by complimenting them on it (ex. I just love when you're confident, chill, etc.). I've used it on her...its pretty effective for short term, getting her to change her mood instantly. I don't think its really effective for changing her as a person. At best I think it can be used to condition her to act a certain way around me, but really thats just around me. My interest is in influencing her as a person for the rest of her life.

2. Compliments: I love complimenting women. If you're one of those people that constantly jab at a woman's self esteem maliciously, we're definitely not in the same school. Compliments also include anything that might be flattering to her (spending time with her, focusing conspicuous attention on her, etc.) I like being romantic, sue me. Anyways, this also works pretty well in the short term, but again, I haven't seen any evidence that it does anything to change her perspective in the long term. And despite what some people believe, it won't hurt to add nice shit to your toolbox.

3. Therapy: I don't know how else to call it. This is the logical stuff a psychoanalyst might try. While it may work well for your male friends, its pretty damn ineffective for a girl that likes you, and actually might make them a little defensive. Definitely don't try this unless your chick is the type that can have logical, self-evaluative discussions with you (I have found some).

These are the 3 main things I've done, and my familiarity with them. I'm going to try a fourth technique. I'm sure its a mix of other techniques that I don't know the names for (patterning, etc.) I'm basically just going to use stories to get past her conscious mind and affect her mood and beliefs. Considering this particular girl has chronic bouts of insecurity, I'll know pretty fast if they work or not. I'll post the results...

No. Your mentality is all wrong. Once you get the girl, you keep her by being challenging, commanding, driven, ambitious. Not by reassuring her you won't cheat on her.

In my experience, this is actually a subtle shit test. She's trying to see how deeply you can fall for her, so that she can regain control of the relationship.

Don't shower her with compliments. Only compliment her when she has worked hard to please you, eg. wears clothes you like, makes you nice food, irons your shirts or gives you a good BJ.

You, my friend, were correct. Since this post, its become clear that the insecurity was a subtle shit test, leading only to even greater shit tests, leading to an attempted coupe de'tat for control of the relationship.

And on second thought, its not really worth being with someone with legit low self esteem. Their perceptions become an ugly reality that I want no part of.

Anyways...enlightment accepted, thank you for the post.

I found myself wondering on this insecurity thing too, and I wonder.. If she has this much insecurities is she even worth being with me ?