A man like this might initially seem to have a lot going for him, but his biggest downfall is that he comes across to women as "too needy."
What are two or three examples of behavior that makes you look "too needy" or "desperate?"
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1 - Calling women way too frequently. You should never, ever call a woman three or more times if she has not yet returned your first call. Huge "no no."
2 - Always wanting to spend time around a woman. Every man should spend "quality time" with their women of interest, but you want to make time for hanging around the fellas or being involved with hobbies of your own as well. It is a "red flag" when you want to spend 24 hours per day, every day, with your woman. Especially when you just met that woman less than a month ago.
3 - Always spending money on women and buying women gifts for no reason. If a woman is your wife or long-term girlfriend, and you buy her nice meaningful gifts to show her your appreciation, that is acceptable. If you met a woman three weeks ago, and you have already bought her a diamond necklace, that makes you look needy and desperate.
You need to GET A LIFE before you invite a woman to share that life with you.
4) You have a demeanor that is so effeminate, that you make women think you are gay or bisexual
Comment: I am just going to keep it real here. I have met some men ... even a handful of my own clients ... who are heterosexual, but they behave more effeminate than some gay men do.
Similar to Factor #3, if women are always complimenting you, and referring to you as a "nice guy," but you seem to always have a problem getting a woman to connect with you romantically or sexually, it might mean that you have too much "yin" and not enough "yang." In other words, you need to present yourself as more masculine.
Step #1: Get rid of the "skinny jeans." Those were not meant for men. Trust me on this.
5) You have "let yourself go" in terms of your physical appearance, wardrobe, and grooming
Comment: As you noticed, this is the exact same "#5 factor" that I used for the women. The reason why is because I see this problem in both older men and older women.
Look at photographs from your high school years and/or college years. Do you look better than when you were young? About the same? Or significantly worse? If the answer is the latter, you have some work to do.
Join a gym or create your own at-home-workout-center. Watch what you eat and drink. Buy clothes that are more flattering to your physical appearance. Read magazines to find out better male grooming tips. Always take care of your personal hygiene.
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I had a frat brother of mine in Chicago tell me last summer, "Man Alan .... I lost forty pounds, and within weeks, women started coming out of the woodworks giving me flattering attention. I couldn't believe it. Sometimes, just losing a few pounds can improve your social life tremendously."