It might work for Frank Reynolds, but carrying around fistfuls of Magnum condoms and sweat wads of $100 bills is (almost) never the best way to get romantically entwined with a lady lying way out of your league. Follow these tips the next time you’re out with your boys and you’ll stand a solid chance of coming up from the minors. 

Dispense with the notion of leagues

This is kind of like the power of The Secret, but less ridiculous. It’s true that if you’re hung up on a girl being out of your league, you’ll surely fall prey to the self-fulfilling prophecy and your unfulfilled privates will be left to their own devices. 

A lot of people will suggest you picture a girl naked, but that’s not going to work here because that’s really just like throwing a 100,000 foot brick wall in the way of your being comfortable around her initially. Instead, imagine her in other, non-sexy embarrassing situations. The best thing you can get her to do is to reveal an embarrassing story from her past. Once her humanity is revealed, your subconscious will recognize that she is not a velvet-lined sex robot from the future, but just a woman. 

Act like you been there

Beautiful women know they are beautiful. And, unless they’re in the same category as Charlize Theron in “Arrested Development,” they’re likely tired of being smothered with visual molestations and stuttering comments. If you want to tell her she’s beautiful, pick one specific thing about her that you like, tell her it’s lovely, and move on. Everybody knows she looks good, so offer a succinct compliment and move on. It’s like this…but less so:

Cultivate a unique value

Woody Allen isn’t the most handsome man in the world. We’ve never seen him without a artfully dischevevled button-up, pearing over too-thick glasses, but we’re guessing Larry King isn’t exactly washing his t-shirts on his abs. Yet, beautiful women are attracted to these men (and others like them) because they know what they’ve got and they run with it. It’s probably no accident that both of those men have money, but we’ll argue that girls like them and they have money because they’ve got talent in another department. 

Larry King is a first class journalist and cultural icon. Woody Allen is a game-changing filmmaker and bohemian darling. They both know it. They both work it like a stripper works the chrome. Find out what your chrome is. Ask former girlfriends and current girl-friends. They’ll let you know what your Trump (another one) cards are so you can play them. When she realizes you’re helping her and making her life better, she’ll want to keep you around.

Show your guts

As many important men have suggested, confidence is your most becoming accessory. Stand with a straight back and your shoulders back. Don’t fidget with your clothes or change your posture to often. Speak slowly and evenly. If you spill a glass or drop a utensil, remain calm. Take everything you’d do normally, and do it at 75% speed. Eventually, ask to see them again for a movie or coffee. Don’t beg. If they refuse, don’t ask again, just politely end the conversation. They may come back later in the night that way, but they certainly won’t come back to a whiny puppy of a man. 

Know your audience

If you’re after a supermodel, you’d better damn well know your way around a camera, around a set, and you better be dressed impeccably. If you’re going after a girl that can shred around 99% of the guys she skis with, you’d better be able to at least keep up. While it’s possible to date out of your league, you wouldn’t go into a genetics exam with three years of Italian under your belt (unless you’re one of these out-of-anybody’s-league girls…). Find out what she is into, and make sure you’ve got your bases covered in that area so you don’t look foolish. 

A good example would be the following. Let’s say you’ve gotten a girl that is fluent in 3 languages to go on a date with you. Nice one. Now, it’s hard to do this kind of prep ahead of time without crossing into stalker territory, but a good prep for that first date is to have at least 3 movies in each non-English language under your belt. Just read the subtitles, internalize a favorite scene, and you’ll have conversational fodder for at least an hour.