Well, hmmmm. We have another reader looking for some specific advice. This one is a 25 year old fellow named S., who has never had a girlfriend, and has only mustered up the courage to ask women out a very few times, always with disappointing results. What's the trick, he wonders.
I used to write quite a lot about dating and my own theories about it. I wrote about how to decide whether to confess a crush, and how to tell whether you're undateable (in 3 parts!). I wrote about chemistry, and how much that matters. Since I've been with NBT these last three and a half years, I've stopped paying attention to all the signals you have to decode to figure out whether a romantic relationship is possible with someone, so I expect Megan will have better advice than me. But ignorance has never stopped me before, so I'll charge in.
There are three things that I used to ask myself when evaluating a guy. We'll take each of them in turn.
1) Do I like, enjoy, and admire him as a human being?
2) Do I want to smooch him? Is he attractive/exciting?
3) Does he make me feel good about myself?
The first question is about personality, morals, values, temperament. On this front, S., I am certain that you are in good shape. Rhubarb Pie readers are exceptionally intelligent, loveable, curious about the world, and engaged with life. Writing to us for advice means you are thoughtful and open to change. It is possible that there are women out there who would not admire you as a human being, but that is highly unlikely.
The next question is about chemistry and attraction. Are you cute? More importantly, do you think you are cute? I fear that you do not realize that you are cute. In your email, you talk about how low your confidence is, and I must tell you that confidence is an important component of attractiveness. Luckily for you, you can get more confident about your own attractiveness. Being attractive has very little to do with your fixed genetic features, and lots to do with what you do with them -- how you dress, how you cut your hair, how you carry yourself. Do you take care of your body? When you do, you'll like it more, just like Megan says, and that will show -- I am starting to do it again and I can attest that when you are getting stronger it makes you more confident and joyful in your social life as well as in your physical life. Do you dress in a way that is flattering and reflects how you'd like people to see you? When you do, you'll carry yourself differently, and you'll feel better. I have learned late in life that there are people who love to think about clothing and style, and they enjoy helping people who don't love these things learn how to dress themselves. Find someone who knows how to do this, and ask for help. Do you know how to flirt? It is terrifying and thrilling to start flirting when it is not your habit, but flirting is a learned skill, and it sounds like you are perhaps a novice at flirting. Learning how to do this is important. You can learn it by watching people who do it. It's a lot like teasing, but with some differences. Make it a goal to practice flirting -- not, at first, with the girls you most admire, but with people where you don't actually intend anything to happen: the clerk at the convenience store, or the librarian who checks out your books, or with a friend's toddler (toddlers are champions at flirting). This is where your homework lies: if you are not confident that you are cute, do these three things. 1) Find a physical activity that will make you stronger, and start doing it, because the progress you make will give you confidence and purpose that others can see. 2) Have someone who knows how help you dress in a way that is playful, comfortable, and flattering. This may cost money, but it is worthwhile. Knowing you look good and that you are making the impression on others that you intend to will help you in lots of ways. 3) Practice flirting, until it is fun, and not terrifying.
The third question is about how you treat a woman you'd like to date. I think it is important to make her feel great about herself. She wants to feel extra-special. Being attentive, being sincere with compliments, anticipating what she might want and making a visible effort to do it for her, those things can make someone feel extra-special, and that feeling is a wonderful gift. You don't want to be a doormat, or elevate her so far up on a pedestal that she can't get down or do anything. But all the little marks of chivalry, sexist or silly as they may be, serve to make a woman feel attractive and a little bit special, and that feeling is delightful. If you help create more of it in the world, you are doing a good thing.