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How to Date Out of Your League in 3 Steps

How to Date Out of Your League in 3 Steps

Ever see an average Joe that you wouldn’t even consider competition arm-in-arm with a partner who is model-material? It’s everywhere these days.  What gives? Some people chalk it up to the old saying “Men want a trophy and women want a breadwinner.” But that’s not the only way this game can be played.

From the woman’s aerial view on a man, it boils down to three things, what I like to call the MAP: Money, Attractiveness, and Personality. Sometimes in that order. But, no one said you have to have all three to get a woman to date you, that’s a triple threat. In this game, you’ll need to play to your strengths and make some enhancements in key areas where you might be lacking in if you want to win over a woman who is hotter than though. Let’s zoom in.


If a man is lacking in anything, sometimes the right amount of money can buy a women’s attention. However, read carefully as this applies to different women for different reasons.

The gold-digger. 

She refuses to try to make her own money and lacks ambition so she craves it in a potential partner−the rags to riches lifestyle without having to lift a finger.  She doesn’t usually need the guy to have a personality either. As long as she gets her Prada purse and Jimmy Choo shoes, she could care less if she ever sees you because it just leaves more time for her to pamper herself. Do you really want this?

If you’re a complete workaholic (which may be how you have so much money in the first place) you may want this part-time partner because you’re priorities lie in your work and your own success, not in her. This match actually works for some people. When you don’t have time for her because of work, you can buy her off with jewelry rather than time and attention.

The ambitious woman. 

She’s got her own stuff going on. Her career is solid. She’s super smart and savvy at pretty much everything. She doesn’t need your money but she likes that you are ambitious and have achieved your own career goals. She wants to buy a house. She sees you as someone she can partner with, not some loser that will drag her down and prevent her from achieving her goals. She’s got a zest for life and wants to experience everything.

Your money shows her that you can take her on the type of luxurious adventures she’s used to including nice vacations and meals that look like they were made on Top Chef. So knowing that you, too, have the same experiences assures her that you may be on the same level life-wise, if not looks wise.


Women think ahead. Some have been dreaming of their prince since pre-school – or at least since first seeing Cinderella. Whether her ideal man’s image was inspired by her father’s looks, or Colin Farrel’s, it’s an ingrained expectation that can be hard to break, but not mission impossible.

When a women agrees to go on a date with a guy that doesn’t fit the spitting image of her dream man, he’s got points docked before the date even starts and he’s got to score a perfect 10 in the other categories. Otherwise he’s eliminated from the competition and no longer in the running for becoming this chick’s next ex-husband.

If a woman doesn’t feel like she’s attracted to a guy, it’s already an uphill battle for him. She’s not going to spend 2 hours on her hair and make-up for the date, 4 hours consulting her friends on what to wear, and 3 days giddy and excited before the date.

Confidence can work magic.

Think about all the ugly guys that have gone far on American Idol and now enjoy swarms of women that would choose them over an Abercrombie model. Ah hah. Since she’s not picturing you holding her in your arms and having your first wedding dance together, you might have to win her over by getting in her thoughts.

Get close to her through the phone.

A woman wants to feel special and listened to. You can work your way into her thoughts and schedule by calling just to say “hi” and see how her day was. She then starts to feel close to you because you care. Trust me, she’s so sick of guys that don’t care and just want to get in her pants. She’s hoping that you’ll make her feel special and that you two might connect so well mentally, that she’ll become more attracted to you. And, yes, if you didn’t know, this does happen with women. Attraction can grow over time. You may not believe this since men either think the woman is hot or not within seconds and that won’t change.

Flirt and keep it romantic.

Or else, you’ll fall into the friend zone fast. I remember going out with this guy who I thought looked a little dorky. We connected so well on the phone and even when we hung out. But, after 3 dates I still didn’t kiss him and couldn’t even picture myself doing it. And trust me, three strikes you’re out.

If you ARE attractive, but are lacking in other parts of the MAP, make sure to school yourself on the tips above, the personality comments below, and try to make some more money, damnit! Looks alone will not always do it these days, at least not for long-unless the girl has major money and no personality.


If all else fails, you can rely on personality. A man that makes a woman smile has a better  chance at winning her heart than one that can’t. A connection is extremely important to most women, often more so than looks or money. Many women have their own money these days and get bored with a guy if he’s just hot and has nothing to say. You’ve got to be quirky.

Play Two Truths and a Lie, Never Have I Ever, or some other get-to-know-you game.  It seems cheesy, and it is, but it works. A woman gets attached to someone she can talk to.  Someone who understands her and supports her. Someone she can lean on for advice and discuss interesting things with. If you can get her to open up, laugh, or fascinate her, you may just be on your way into her heart! When you’re talking to her, make sure you’re asking her more questions than she asks you.

I remember in one of my multi-dating phases, I was hanging out with one guy that was super hot and another that was more fun. At first I was more excited about the hot one but then when he wasn’t trying as hard and didn’t have anything interesting to say or do, I became way more into the one that was fun and calling often to say, “Hi” even though he wasn’t as hot. He was interesting and brought out the best in me and made me smile. Women typically love attention and, unlike most men, can grow attracted to someone in time.

So, there you’ve got it. The MAP. If you’ve got all three, lucky you! If not, I hope this MAP helps you find your way into the heart of a hottie.

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