What is challenging for one man may not be so difficult for another. A virgin might think that getting his first lay is the pinnacle of achievement, but to a singer in an indie band with excellent emoting skills getting laid is an afterthought. There are some challenges however that are difficult to accomplish for almost all men.
Converting a lesbian
Not a bisexual girl. Those are a dime a dozen. I mean committed lesbians; the ones who have never been pierced by man love and know as much about cabinet resurfacing as Bob Vila. Turn a decent-looking scissor sister into a traitor to her orientation even for one night and you will have earned the respect of your peers. Bonus points if you pick her up at a Vagina Monologues show.
Yeah, it’s cliched, but that doesn’t change the fact that despite the braggadocio of countless pornstars in their own minds this accomplishment is pretty rare. If the average American man has seven lifetime partners it’s a safe bet that he didn’t blow the bulk of his lifetime wad on three nights with six different women. Pull a threesome and your name will echo throughout the realms. Film it and it will echo throughout YouPorn.
Having sex with a religious girl in a place of worship
Sure, repressed Catholic girls will hike their skirts in the back seat of a car under the watchful eye of St. Christopher, but try and get her to renounce her chaste ways in an empty church pew or in the rectory while a six foot tall crucifix gives her the stink eye. Ditto for other religions. Ever bang a Jewish girl in a temple? A Buddhist in a monastery? Or… wait for it… a non-Americanized Muslim girl in a mosque? You do the last and manage to avoid decapitation your name will be legend and spoken of in hushed tones around campfires and at men’s retreats.
Staying in love
Falling in love is nothing special. People do it all the time. Staying in love, and having it reciprocated just as strongly, is another trick altogether. Don’t listen to the rainbows and unicorns brigade; the world is not awash in a field of love consciousness. It is instead awash in fear, hatred, anger, jealousy, duplicity, lust, ego… and occasionally love. There is a reason so many people yearn for the life-giving power of requited love and that is because it is so rare. Stay in love with a girl who loves you back and you will secretly be hated by everyone. Kind of like lottery winners.
Having sex with a girl who is already in love with another man
Why is this so hard? See above. As extraordinary as deep long-lasting love is, seducing a girl in such a state away from the object of her love for an illicit tryst is rarer still. Even the best players advocate learning to recognize the signs of a girl in love with her boyfriend and moving on to more pliable targets. A girl in love gives off a vibe that screams “I don’t even notice other guys”. Try and overcome *that* bitch shield. This is the Holy Grail of male challenges, and if you accept this challenge and succeed your name becomes a powerful symbol of evil in the world, scribbled in angry lettering on the back of notebooks by ostracized goth kids in high schools everywhere.