A PrettyBOY's Blog: Dating A Tomboy.

It’s always a bad idea to make rash generalizations about a certain group of women, and the tomboys have to face an onslaught of false assumptions. They may enjoy more masculine pursuits; they might prefer to take in the Patriots game than go to the spa; they may have more guy friends than gal friends. Perhaps they’re athletic and willing to scale a sheer rock face leaving men in panting pursuit (an intriguing situation), and maybe they don’t wear skirts; but they still look fantastic in the club, and you want a legitimate shot at meeting women like this.

There are certain ways to go about scoring such a woman, and many of them revolve around your ability to be tactful and candid. You have to prove you don’t believe in the stereotypes, you have to be sensitive to their sensitivity, and above all else, you have to be realistic. If you look at this from a straightforward perspective, scoring a tomboy is not quite so complicated.

She’s also a woman

She may be able to hit a baseball, but that doesn’t stop her from being a woman. Perhaps the No. 1 stereotype all tomboys encounter is that men believe the athletic girl has “one too many X chromosomes” or some such nonsense. As a result, they may believe she has no interest in things like romance and passion; she’s too busy riding mountain bikes or camping out in front of the tube on NFL Sundays. Now, while she may indeed be averse to frilly, lacy pink-colored stuff, she’s still a woman who deserves to be treated like a woman. If you show you’re willing to treat her like the lady she is, you will score big points for seeing past the whole tomboy image. You will show off your respect and sensitivity, and she won’t have to take your hand and lead you to the truth.

Indulge her hobbies

OK, so she enjoys the outdoors -- take the opportunity to express your interest in similar activities; it’s an obvious opening if you’re in pursuit. If you opt to go for a long hike, there won’t be anyone around for miles and…well, it’s another potential gimme. Stand up and participate in her hobbies, and the results should be undeniably positive. Besides, if all you have to do is hang out with her and watch sports, why would you ever complain?

Flirt with her competitive side

Whether it’s predicting the outcome of the NCAA tournament or doing her damndest to top the boys on the court, this girl very likely has a healthy competitive streak. You can use it as a springboard to landing some one-on-one time (pun intended). Maybe she’s bragging about her arm -- “I was a hell of a softball pitcher in college!” -- and you quickly reply with: “Think you can get it by me?” Offer to play her at her favorite sport, and to up the ante by appealing to that competitive nature by challenging her to a true-blue contest, no holding back. There are any number of activities and opportunities involved in this tip, and you only need to get her talking about her favorite hobbies. It doesn’t even have to be something athletic; her competitive instincts could extend to just about anything, so you could throw down with a match of “Twister.” You may not be quite so lucky, but you get the gist.

Be impressed

If she’s the type of woman who won’t respond to compliments centering on her physical appearance, switch gears. If she’s heading out on the weekends and trying new things, ranging from kayaking to skiing, that means she has a certain amount of dedication and determination. If she tells you about how she gets up every morning and goes for a run (regardless of the weather), don’t miss the opportunity to be duly impressed. Furthermore, you can outline the obvious contrast when comparing her to other women; in your eyes, it’s refreshing and appealing that she’s so committed to sports or the outdoors. Women love to be told they’re special -- provided you can convey your appreciation correctly.

There’s no such thing as an unapproachable woman, and even though the tomboy presents you with a unique set of obstacles, scoring the target just requires some courage and observation. Don’t be afraid to offer up your pride as an agreeable sacrifice. Above all else, don’t make snap assumptions; she’ll relish shooting you down. Being a nice guy, as always, is the best place to start.

Fun for both of you

Unlike many scenarios the Player finds himself in, scoring a tomboy is one where you don't have to pretend to be interested in things that you could care less about. Having interests in common with a woman -- whether it's fitness, a sports team, or just life philosophy in general -- is something to take a moment and appreciate.