[LordSappington]

I'm 5'5", and I can hold a conversation with some women. I weigh a bit more, at 145 lb. While there's nothing you can do about your height, if it concerns you about your weight, do what I did and hit the gym to put some weight on. It will boost your self esteem and make you look better and feel better.

I'm going to disagree with this whole, "Talk to other people about them" advice. It works alright for maybe 5-10 minutes, when you go through the basics: "So, what do you do? Where did you grow up? What do you do for fun?" After a while, it feels like a game of 20 questions with you giving very little back. Most people I've met do not actually like talking about themselves in the way that I initially thought about. Many of them don't even ask the appropriate question back, "Oh, I'm an accountant. What do you do?" I'm not saying this advice is bad, but there is a tremendous amount of stuff people neglect to mention that is involved, most likely because, for them, it's all unconscious.

You have to identify something in them that they get really excited about. This is not likely to be the basic questions about them; you have to delve a bit deeper into their passions. This can be very hard to do because many people are resistant to opening up like that. The key is that you have to get them interested in you. One easy way of doing this is showing true interest in them like other said, but this is not enough. They have to view you as a fun and interesting person as well so the conversation becomes two-way other than you just pestering them.

I've found that the best way to do this is stories. Think about your life. Think about something interesting you did or read or saw. Now write down that story. I read a lot about a wide number of topics and can often pull out random anecdotes about anything (I once had a long conversation with a plant biologist about bananas... I had just read a long article about the history of the banana). You also have to fill your life with interesting things. If you like cooking, cook a lot and experiment. If you hate dancing, go dancing to experience something new.

When you've done all of that, you will become an "interesting person" and will find conversation much easier. This is not easy to do. It requires a lot of hard work, and it's frustrating to see so many people do it naturally.

For now, I recommend that you find a bunch of canned stories. Think about the last 5 women that you met. Think about something they said that you can relate to. For example, maybe she's an accountant, and maybe you had an amusing run in with the IRS. Maybe she likes horses, and maybe you got into a debate with a friend over the silliest horse name. Write those down. And use them. At the end, say something like, "Have you ever had something like that happen to you?" or "What do you think?"

If you meet someone new and don't have a story available, then do your best without it and then think of one when you go home. At the end, you will be full of all sorts of interesting things to say. Really, these are just tricks to get her talking. Once she's talking, your true conversational skills kick in, but I've found that most people who are "shy" can open up pretty well in a truly engaging conversation. Sometimes, conversations start dying. In this case, just abruptly change the topic and tell your favorite story. If she still doesn't respond, politely leave the conversation... she's just not interested. Don't take it personally; she may be in a bad mood or she may just be a boring, self-centered person.

Finally, practice, practice, practice on everyone. Men, women, children, whatever. If you hit one a day, in a year, you will have 365 stories to tell and you can talk to pretty much anyone.