I'm very secure about myself; but insecure with my place in relationships, regarding the other person's interest and, specifically, ability to understand me. I've had little flings with no substantial intellectual / emotional connection, one unhealthy relationship that I ended several years ago, and have dated some really nice, very "agreeable" girls but the connection wasn't right because they were either too immature or simply lacked compatible emotional maturity and depth.
I often wonder and have seen myself with an older gal, though not by much. Who knows. One thing I've taken a note of is my inherent tendency to idealize women and the relationship or "situation" itself, and my tendency to "lose myself" in the other person, something I am now very conscious of. With all of my experiences in hand, I am equipped to handle dating better than before I think, and I'm optimistic about new experiences. I will always take care of myself first anyway.