Bro on a Mission to Sleep With All of His Female Co-Workers Gets a Dose of Reality

By 11.07.12

Q: I work at a place that's is predominantly girls and I, being the ambitious man I am, decided to make a list of about half of the girls. This list is for “extracurricular activities” with said girls. There are nine girls on the list (and still counting due to new hires) and after about four months of working there I have gone through three girls. I have already gotten the “go ahead” from two other girls. That leaves four girls probably five including the new hires, I would really like to complete my list but I don't want the other girls to find out because some has already leaked. Any tips on how to make sure it’s kept on the DL. (My male coworker and I started the list and I am not really that proud of it but I am physically unable to turn down a challenge ,especially of this caliber).

A: Do you honestly believe that you'll be able to “keep this on the DL”? Allow me to burst your bubble of ignorance by telling you that you simply cannot, because this is going to come back to bite you in the ass, and then cut your dick off.

Make no mistake that circa halfway through your list of intended conquests, rumors are going to start circulating– and soon enough, you're going to be pussy blacklisted. You heard me, motherfucker. Lists that long and interrelated should be reserved for the grocery store only.

Quit double dipping and treating your workplace like a Mormon compound. Focus on working while at the office, rather than fucking all the people who work there.

Q: I've been dating my girlfriend for about 2 and a half years now and her birthday falls on Thanksgiving. I'm going to Thanksgiving with her family, and I have tickets to a concert the next week for us (which she's known about for a while). I have two questions. First, my family is apparently more outgoing and will joke about a lot more than hers. Should I try to be the star and try to leave an impression, or do I hold my tongue and nod politely? Second, because I have the tickets, is it expected that that is her birthday present, or do I still get her some small things like card/candy etc?

A: In regards to Thanksgiving behavior, find a happy medium between total silence and your normal outgoing personality. Avoid being over -he-top, because aside from being boring, a family of squares can be judgmental too.

As for your birthday gift, I appreciate the thoughtful gesture, as I'm sure she will. Yes to the card, replace the candy with a romantic dinner before the concert. Wrap the night up with some mind-blowing sex and you should be good to go.

Q: The way things are going these days with texting completely dominating all communication outside of work, what is your stance on asking a girl out via text message? I guess I would consider myself to be old school and opt for the phone call. Do girls respect that or see a call coming in rather than a text as completely out of the blue and catch them off guard?

A: While I'm non-traditional in many respects, the advent of the text message has in my opinion thrown quite a wrench into the world of dating. If you text her to ask her out, you can come off shy or unconfident–aka it could be a turnoff. Not to mention, if she never answers you'll never know if you have the wrong number, she lost her phone or she simply has zero interest in going out with you. That's why I recommend the combo platter– text her early in the week (Tuesday or Wednesday is ideal) asking if she's got any plans for the weekend, and that you guys should hang out. When she responds letting you know how available she is, give her the heads up that you'll call her this weekend–then do the traditional dialing come Friday.

Q: After sleeping with a girl is it offensive to ask her not to tell anyone? I recently slept with a girl who is friends with another girl I like. I’d prefer if the girl I like did not find out about it.

A: In short, yes–after adding another notch to a girl’s belt, it is absolutely offensive to make that kind of request. Obviously situations occur where this sort of statement is necessary– a recent breakup, ex hookup or disapproving friends. But if these grounds haven't been mutually acknowledged beforehand, chances are her feelings are going to be hurt. Consider this ahead of time– before you even persuade her back to your place, you know if you'll eventually ask her to keep it a secret. Solution? Stop settling and hook up with girls you actually like, who don't have excessive baggage attached.

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