It's been five years since my first real romantic relationship. It was in college, lasted three years, and she was my first sexual partner. She was a very "marriable" type for me, but during our relationship she broke up with me three times. The fourth time, I felt like I had had enough and we parted ways. She had some insecurities and trust issues, probably due to her father's alcoholism, and the terrible divorce that occurred when she was 12. She still despises her father in a lot of ways.

Ever since then, I feel like I've been chasing after alcoholics/codependents or broken women who fall apart at the first sign of something real, or they play games with me and perhaps several other men. Most of these women I probably wouldn't end up with for the long term, and I know that. I almost never have any sexual contact with them, but we tend to get close, intimate, almost like we're in a relationship, just without the physical aspect. These women then tend to sleep with losers, old men and assholes while they reserve their tender feelings for me.

When a woman who is together, secure and on track with her life approaches me, I get bored pretty much right away, and blow her off. I want to change this pattern, but part of me wonders if this is due to a resistance that I have to growing up, as is the case with other aspects of my life, or if the problem stems from something else that needs to be addressed before I can have a real r...

Me giving advice on attraction to unavailable partners? I should change the name of this column to Blind Leading the Blind! I kid, because, lucky for you, the deal here is that I pass along the wisdom of other people, and I’ve found you some experts who, unlike me, might not have their own history of chasing after romantic mirages (but who knows).

Psychotherapist Margaret Paul, author of “Do I Have to Give Up Me to Be Loved By You?,” took a look at your email and picked up on a fear of intimacy, which she speculates is likely tied to abandonment and "engulfment issues." Don't be scared of the pathologizing language: This is a classic relationship dynamic, and one that perfectly describes the dating experiences of most 20-somethings I know. One partner has a fear of abandonment or inadequacy, which causes them to push for more and more intimacy, and the other has a fear of being smothered in the relationship, which causes them to pull further and further away. "He sounds like he is operating from his own woundedness, and instead of learning how to take loving care of himself, he caretakes these damaged women, which gives him a feeling of power," she says. "This isn't going to change until he does the inner work he needs to do to deal with his fears."

Frances Cohen Praver, a clinical psychologist and author of “The New Science of Love: How Understanding the Brain’s Wiring Can Help Rekindle Your Relationship,” says we are often “attracted to some aspects within ourselves that we have denounced.” For example, she explains, "If you are damaged in some way, with self-esteem or insecurity issues, and less than optimal childhoods, you may disavow those parts of yourself and take on a persona of a confident, secure, solid, strong person," Praver says. "And so you attract a powerless woman who needs your strengths to complete her. You then live vicariously through her powerlessness and she lives vicariously through your assumed power." The kicker: "In time, however, she finds her own power, dumps you and you fall apart in a powerless heap."

During turmoil in my own past non-relationships, I would wryly explain to friends -- much as you have to me -- that, “Oh, well, he’s broken” or whatever other dismissive diagnosis I’d come up with. I later came to realize that it was a cocky and arrogant display of faux self-awareness. The underlying message was, “I, however, am perfectly healthy and normal.” It was defensive, avoidant and an attempt at control -- and the same is often true of the pursuit of unavailables in the first place. Chasing after a relationship requires much less vulnerability and emotional reckoning than actually being in one; and, unlike “broken” partners, "together" ones have the ability to reject us in a meaningful way, and that can be downright terrifying.

The official prescription from the experts: Spend time working on yourself, instead of trying to fix and win over these unavailable women. Examine the reasons why you might be avoiding intimacy (therapists are awesome for this) and try to make yourself more available. In time, says Praver, “you will attract and love the right kind of woman."