This email from Tim recently arrived with the subject heading Dating Advice for a Loser. Immediately I was saddened that anyone would label themselves this way, but as I read the letter I felt that Tim has real potential and might benefit from the collective wisdom of the HUS crowd. He sounds prepared to accept reality, to some extent already has, but needs a starting point. For ease of reading, my feedback is interspersed throughout the body of Tim’s email.

My name is Tim, and I’m a 39 year old male who hasn’t had any luck with women for more than 10 years now. I’m not very good at flirting or asking women out. I’m a naturally shy guy, and I’m a bit eccentric to boot. I’m pretty nice, though. Strike 3, right? I probably come across as slightly awkward and quirky. I feel like I’m 17, although when I really was 17 I was quite immature and had some idealistic visions about what girls were like and what they wanted that have turned out to not to be true.

SW: Right off the bat, I can see that you’re in need of swallowing the Red Pill, which is a metaphor for the truth about female sexuality. Mating is a brutal process where women winnow out men who they perceive have inferior genes. Good genes are defined by evolution as conveying social dominance, first and foremost. Women also select for compatibility and other long-term positive traits, but making the first cut will usually depend on a self-confident display of maleness.

Some women do aspire to and even achieve feminine ideals, but they are increasingly rare in our culture. It’s important to qualify women according to your standards, and avoid putting them on a pedestal.

I can change. I know it. I already am. I’m getting my life together – I’m about to get my graduate degree in teaching and my first-ever good job next year (2012). I’m taking better care of myself and my house, I’m socializing more, and I’m seeking out dating advice from a few friends, female and male.

SW: You have a very positive attitude, and have already made enormous changes in your life. It sounds like you have some momentum and are moving forward towards your goals. This is a great time to learn about women and begin to put your knowledge to good use.

I recently asked a young woman out. Her name is Kat, and she is probably in her early to mid-twenties. I met her at the local swimming pool, when the teacher I’m doing my student internship with brought our class down 4 times a week. I noticed how pretty she was right away, but I didn’t stare. Over the next several weeks, I couldn’t help glancing at her as she taught some of our kids. She has a beautiful smile, and she genuinely seemed to enjoy working with the kids. I noticed her glancing back at me. I didn’t want to creep her out, so I tried to minimize this, but often when I looked at her, she looked at me.

SW: Mutual, sustained eye contact is a definite indicator of interest. It’s good that you were sensitive to the possibility of creeping her out by staring at her without any indication of mutual attraction. The fact that this phase lasted several weeks is not good – you dithered. Ideally, you would have escalated by teasing, flirting, or interacting in some way. I understand that may sound like an insurmountable obstacle, but you can learn to flirt, and you need to do so.

From a female point of view, your keeping some distance/not making any kind of move would have been a strong indication that you were unavailable or otherwise disinterested. I can tell you that I’ve heard and even said, “He stares at me all the time but he never says anything!” hundreds of times. What you know as approach anxiety will mystify a woman, especially if she finds you physically attractive. Most of us just don’t understand how paralyzing shyness plus the risk of rejection can be.

One day as class was letting out, she came up to me and handed me the report cards she was giving the kids on the swimming progress. I couldn’t think of anything to say, even though I had been planning on telling her what a good teacher she was, both because of her great smile and the way she worked with the kids. I was dying to talk to her to see if she was at all interested in me, an older, shy guy. But did I say anything? No. I just said “Thanks” and tried to smile weakly. I can’t even remember how she reacted. We went our separate ways. We both had jobs to do.

SW: Tim, you need to learn about Game and you need to practice, practice, practice. This is very hard work but the men here can tell you that it is worthwhile and can change your life.

I made up my mind to approach her at the next lesson. As the lesson was ending and she was getting out of the pool, I approached her and said, “I just wanted to let you know what a great teacher I think you are.” She smiled and said thanks. I told her that a big reason for this was her great smile, which the kids really seemed to respond to. Then I stuck out my hand and introduced myself. Again, I can’t remember how she reacted, but we both had jobs to do, so I said, “Well, I’ll see ya later.” I remember she responded with, “Definitely” as we went our separate ways.

SW: A positive development, but too little too late, I fear.

The last swimming lesson was a free swim with both 4th grade classes. The atomsphere was fun and not as serious like the swimming lessons had been. I was asked by one of the teachers to take pictures of the kids as they swam. I tried to flirt with Kat by showing her some of the pictures of the kids swinging from the rope swing. She seemed to enjoy this. I also took a picture of her as she swang, and showed this to her. Again, she seemed to enjoy this.

SW: Good, you found a way to interact socially, and you succeeded in flirting! Cameras are good – taking pics and sharing them is a whole lot easier than thinking up small talk with someone you don’t know.

I really wanted to ask her out at this point, but I couldn’t figure out a good time to do it. We were both at work. We exchanged glances as I left for the day, glances which seemed to me to say, “Ask me out!” Maybe not. I have no clue, really.

SW: Here’s where I want to hit you over the head! It sounds like she was standing there willing you to make a move. And you didn’t do it.

I decided to go to the swimming pool as soon as school let out. The problem was, I had the feeling that she was getting off work just as we were leaving the pool. I did go to the pool after school, about an hour later, but was told that she wasn’t at work. The gal behind the counter, who was also a swimming instructor and who knew I was, asked if I wanted to leave message. Against my better judgment, I asked Kat out on the note and left my phone number.

SW: Ouch. You should have trusted your gut instinct. I think this move signaled weakness, but the biggest problem is that you ceded all control to her.

That was last Wednesday (May 25). I haven’t heard a word. I figure one of several things is going on:

1. She’s already taken (boyfriend/husband; if she’s married, I’m guessing she doesn’t wear her ring in the pool).

SW: I doubt it. If she is, she shouldn’t be sending out those sultry stares. It’s possible she’s looking for some on the side, in which case it’s good you escaped her clutches.

2. She thinks I’m too old for her. I’m 39, but people often think I’m a good 10 years younger than I actually am both because of my boyish looks and personality. I probably don’t act like a confident 39 year old. My hair is slowly graying on the sides, although I keep it pretty short and it’s hard to tell from a distance. Maybe she only realized that I might be older when she saw me up close?

SW: You are a little old for her, especially if she’s in her early 20s. The rule of thumb is half your age +7, so 27 is about the youngest you should be aiming for. I don’t buy the idea that she lost attraction when she saw you up close, because it sounds like the sexual tension persisted after you spoke.

3. She’s not attracted to a guy who isn’t very confident around her (I’m guessing she percieves me this way).

SW: Bingo. Women prefer confident men. That’s discouraging for men who don’t feel confident, and “Be more confident” is not helpful advice. The good news is there are specific behaviors that signal confidence. Flirting in and of itself serves this purpose. This is a skill that can be learned.

The bottom line is that if you don’t think you’re all that, she won’t either. By the way, women love men who are good with kids. It gets us thinking “dad.” Since she obviously enjoys working with children, she’s bound to regard a male teacher positively.

4. She’s not attracted to a guy who asks her out using a note.

SW: Not unless she’s in sixth grade. From a 39 year-old man it’s incomprehensible. It displays enormous vulnerability, and this is a major red flag for women.

5. She’s not attracted to me because of other reasons (I’m short, 5? 6?, 150 lbs., muscular, but she’s shorter, and she’s not rail thin herself).

SW: Nah, I wouldn’t worry about this. Plenty of guys with Game do fine with your physical attributes. Are you going to be a chick magnet based on your physical traits alone? No, but very few men are. If you’re muscular, that’s good, it sounds like you are in good shape. What’s most important is how you feel about yourself. Women can sniff that out without even realizing what is turning them on or off.

I’m not sure what to do at this point. I know I shouldn’t, but I think about her night and day. I pine for her. My mind knows I shouldn’t, but my heart won’t listen (I’ve always had this problem).

SW: Uh oh, you’ve got her on a pedestal. Face it Tim, you don’t even know this woman. You have only the most cursory observation of her to rely on. Your one-itis is clearly a projection of what you want her to be. That is not real. You should make her qualify herself as a potential partner – that is the right mindset.

What I’d really like to do is to go back to the pool with some of the pictures from the free swim, give them to her, and ask her out again in person, realizing that she might say no.

SW: Well, you have nothing to lose at this point, so why not? My sense is that you will probably need to let this one go, but why not practice the ask and learn from the experience. If you do decide to do this, I would not even reference the note. Pretend it never happened.

Alternatively, I thought of writing her a short note on nice paper containing the pictures and telling her that I understood she wasn’t interested, but that I thought she was an interesting, nice person and to not settle for anything less than a great guy, something nice and positive (and true) like that, and give it to her either in person or not.

SW: No! Do not do this! This is supplicating behavior. You are the great guy. Never give someone positive feedback for not being interested.

Another option is to go swimming at the pool when she’s there, and either ask her out or just try to get to know her better. Gotta stay outta the friend zone, though, right?

SW: This is a good idea, but ideally would have occurred early on. Again, you have nothing to lose. If she is not interested, you’ll know immediately. She’ll make herself scarce and avoid you. Reestablish rapport before making any kind of a move. I’m not sure how the note would play into this scenario.

What do you think? Am I coming on too strong? Not strong enough? Innappropriate time/place? Should I get to know her better? I figure the best I can hope for is that she recognizes that I’m a shy guy trying hard.

SW: That is not the best you can hope for. That is the kiss of death for most women. You need to be a confident guy not trying very hard at all.

I have a lot to offer a woman, I know this deep inside. I guess I really want to talk with her in person one more time before I give up. I feel strongly enough about her that I feel I owe myself that much. At the least, talking with her might let me know whether or not she’s taken already. I’m not asking her out just because she’s young. I’m also attracted to women more my age. Maybe I should just forget about her? This would be difficult, but not impossible.

SW: I’m glad you know your worth – confidence comes from that place. I’m a big believer in saying what you need to say. Go for it if you want, just be prepared for rejection and resolve to learn from it.

Thank you for your blog. I love it. When I found your blog, I felt as if I finally met a woman who understands men. I get so tired of hearing “just be yourself” when this obviously isn’t working for me. It is hard for me, though, to hear what women find attractive in men, because I feel I’m not a lot of those things, but I’m going to try. I’m tired of being lonely, and I have a lot to offer a woman! I just know it!

SW: You are very welcome. I agree that “just be yourself” is worse than useless – it’s counterproductive. Many men waste years feeling like they are failures with women, wondering why “myself” isn’t good enough.

While your situation might seem desperate, I actually found quite a bit in your letter that is promising for the future. You seem to have some awareness of what you’ve been doing wrong, a very positive attitude, and have taken several concrete steps to develop yourself and improve your life, which is great.

The bad news is that you’ve got a long journey ahead of you to realize your objectives. The good news is that there is a map that will show you the way. At 39, you’re still in your prime, and especially if you are attracted to women your own age, you can expect a lot of improvement if you get some Game.

As a starting point, read some of the Being Male blogs on my blogroll. Several of them focus on Game as a way of finding the right woman for a serious relationship or marriage.