Stop Trying: When Not to Hit on Her

She’s Your Roommate’s Guest

Yes, this past weekend I had the luck of passing out on the couch of my old college buddy. After smoking the hookah, downing my girly Bacardi silvers, and watching the Pats lose, I had blessedly found sleep when the sounds of my buddy & his girlfriend finally died down. Then, in the dead of night, who should appear and ask me to share his bed? The roommate. This was not happening for two reasons. One, as a guest, the girl is usually there to crash. She has no other options at the moment and is actually there to sleep. Being too tired to make it home usually means she is too tired to provide the entertainment you deserve. She will only be annoyed if her sleep space is invaded by sexy time. Women are finicky about when and where anyway, so she will decide you’re an asshole for no other reason than she’s tired and too drunk to find the subway. Reason two is this: you’ve probably just met her. She may even be the kind of girl who will go home with a stranger in a bar (in which case, invest in anti-biotics), but that likely still means she won’t do a complete stranger who happens to share the bathroom with her buddy.

BONUS: If you can refrain from hitting on her the first time, you will get to know her the next few visits, and she will certainly consider you and may even initiate something on her own. Girls love their friends’ roommates. Once they know them. The first time, she probably is still getting your name down (I was still referring to him as “hey you"). So play it cool until you’re sure she’s visiting as much to see you as your roommate. It’s like finishing off his Chinese food the next day, and it even gets delivered. 

She’s Vomiting Drunk

Mmm... tastes like romance. 

You think this is a no-brainer? How many guys have done this in my younger days, I can’t tell you. Men like to be really, really sure a girl is drunk sometimes, and this is apparently a good litmus test. The girl will categorically refuse. She will also equate you with a feeling of nausea when she looks back on this (we remember a lot more than we admit to), and this can’t be sexy. Offering her water or somehow getting rid of her/putting her in a cab is a better idea than, in between heaves, telling her how much better she would feel if she took her clothes off (oh yes: true story). Stop trying. Take her to brunch the next day instead (tell her the "hair of the dog" line) and only allow her to get a little buzzed on the bloody marys before suggesting dessert that night.  

She’s Buying a Pregnancy Test

"Well, I guess I can't get double pregnant.  Let's wait to see what the indicator says at least." 

Yes, the girl probably gets around, and that could include you, but she may not be so in love with love at this moment. Just a hunch. 

She’s Just Dumped You

You are feeling low, and you do need sexual healing. Begging for a pity fuck/goodbye sex not only won’t work, it might piss her off too much to come cry on your shoulder when her next guy doesn’t work, which is really a better time, isn’t it? The key in all these scenarios seems to be patience. Because women love foreplay, and foreplay = waiting. 

Alternately, if you’ve just dumped her. If you’re one of those men who breaks up with his girlfriend, and before he waits for her to finish sobbing, tries to unhook her bra-strap, you might want to wait until SOMEONE ELSE has made her cry before doing the big over-under. If you absolutely can’t wait that long and don’t have enough money to get someone new drunk, make sure you are crying too. That is called make-up sex to her and break-up sex to you. Be sure not to let the door hit you on the way out when she realizes this. 

Hitting on her fter her friend has just dumped you, or you have just dumped her friend, can actually work, because some women are sly bitches. You may have to cry again. 

The STD Testing Clinic

"Actually, I was just thinking about all my mistakes... what brought you here, anyway?"

Especially if she’s just dumped you.