I received a question recently from one of my male readers. He had a fear of asking a girl out that he was really into. His worry was that she seemed way out of his league. He described her as tall, beautiful, successful, and extremely sweet. This guy was average looking, had a decent job, but was clearly lacking in the confidence department. There is definitely such a thing as a “mismatch” when it comes to dating. However, there are times when you may be able to have a chance with a girl that you never imagined…
If you live in a city like New York, the ratio of women to men is ridiculous. It’s amazing how many beautiful and smart women are still single. It’s not because they are flawed, it has more to do with the fact that there is so much opportunity it’s hard for guys to make a decision. Women naturally want to be courted and be treated like a princess. If you are really interested in dating someone that you think is out of your league, start off with showing her attention. Don’t buy into the concept that women like jerks. If she responds to your actions positively- go ahead and ask her out. You have nothing to lose. Honestly, what’s the worst that can happen? She says no? You have to take chances in life and not worry so much about rejection.
Years ago I used to attend classes at Hineni with Rebbetzin Esther Jungreis. Talk about a singles scene! At the time I was in a relationship, so was not interested in anything other than hearing the weekly Torah portion. I have to say though, I was blown away by the confidence some of these guys had! I am 5 ft. 10 and I would have these short, nebbish type guys make a “B” line for me to ask me out on a date. Although I was not at all interested, I thought it was awesome that they were not afraid to be rejected. My response was always sweet and I made sure to never make them feel embarrassed for trying. I really respected their efforts. I am sure though, that after doing this with enough girls someone had to finally say yes!
If you don’t like the direct approach, you can be a little more subtle. It just will take more time to get the desired result. For instance, if you meet a girl out in a social setting and you want her number- strike up a conversation and give her your business card. Then say “do you have a card too?” Usually when a man gives me his card I feel obligated to give him mine. Once you have her contact info you can follow up and tell her it was great meeting. Take note of her profession and email her an article or something relevant to her interests. Once you develop a rapport, invite her out to a social event. It could be a dinner party, charity gala, or friend’s birthday party. This is a great way to take her out amongst friends and it doesn’t come across as a formal date.
Whatever approach you take is fine, just don’t let the fear of rejection take over. Honestly, what’s the worst that can happen? She says no? After doing this with enough girls you will eventually get one that you want. There’s an expression that goes “Throw enough %#*@ against the wall and something’s got to stick” so don’t hold back…your beshert is waiting.
If you’re a woman reading this, you should check out the flip side of this post – Is He Out of My League.
Do you have any thoughts on the subject or experiences you’d like to share? Please do so in the comments section below. And if you have a friend who might benefit from this post, please share it with them.
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