How do I start a relationship?

I’ve never been on a date or had a relationship, never even been “out” at a club or anything. I’ve been moving around for most of my life and I have never managed to keep hold of the friends I make. All that makes me pretty socially incompetent. People like me to be friends, but I wouldn’t know the first thing about starting a relationship.

I really like a girl who goes to this college. We’re on the same bus, offer each other lifts if we can. But when we do talk our conversation rarely gets into anything personal. I’m at a loss. I have no experience and no one to turn to for advice. I would greatly appreciate it if you could help me out here. I would like to have a social life as well as a working one.


Everyone has some kind of emotional baggage that seems to inhibit relationships from succeeding. Yours is just more clear to you. And it is getting in the way of relationships starting. The clarity of your baggage is actually a benefit. Everyone eventually needs to overcome their baggage. Many people aren’t even aware of having any. You are ahead of the game. Out of inner reflection, which is a beneficial component of introversion, you can more clearly see your inhibitions and where you lack experience socially. So you have a clear area to focus on for your own personal growth.

The deal is this. What normally holds people back from doing the personal growth involved in overcoming emotional baggage is one thing: fear. It takes courage to deal with the discomfort of doing the personal growth. In your present case, it takes courage to deal with the internal discomfort of extending the talk with this girl into a more personal arena. Know that you CAN move through that discomfort. But it will not be comfortable doing so.

It’s kind of like standing on the end of a diving board. You can stand there as long as you want. At some point, though, you are going to jump. I once knew an excellent diver. He told me he would envision how his dive would be. Then he would jump. You can use this same idea — inner visualization of the outer results you want — as a tool in your quest. This is how it would work, if you want to create and use this inner tool:

Envision in your mind a picture of how you ideally would want to look if you were having a conversation with this girl on a more meaningful level. Relax and see that picture in your mind. As you gradually envision this inner picture, feel free to change it at any time to make it look exactly how you want it to look. See it with you looking friendly, open, and, perhaps even confident and having fun. Maybe not all those things at first, but over time add them in just to see how they look.

I suggest you make this an inner practice doing this visualization for awhile, say ten minutes each morning and evening over the next week. It may be hard to get into it at first. The image may be clear — or fuzzy. No matter. Go with whatever you get. There is no “right” way to do it. But if you stay relaxed with this inner practice for a week, you might be surprised as it gets easier to see and enjoy watching that visualization.

When you have done this for a week, and you have an inner picture that is looking the way you want it to look, email me and I’ll tell you the next step in this inner-confidence building practice.

And, of course, if you just want to jump off the diving board at any time and initiate a deeper conversation with the girl, feel free to do that. It can be as simple as talking about things that affect each of you emotionally. Like school. Or world events. And just allow time and space for her to share her feelings. And respond with understanding. And respond by sharing your deeper feelings.