Category: Ask the Urban Dater

Ask the Urban Dater: I Want My Girlfriend to Have Sex With Someone Else

Hi I'm 28 years old I have been with my girlfriend for 5 years. We have a great sex life I do however fantasize about her and other men. I don't want to see her have sex with them, I...

/ March 13, 2017

Ask the Urban Dater: Is the Grass Really Greener?

My boyfriend's best friend just became single. He is embracing his new freedom by drinking, partying, & constantly talking smack about his ex. (who I think, she is completely reasonable in this whole situation) Now my boyfriend said every guy...

/ September 1, 2015

Ask the Urban Dater: The Job Seduction Edition

New Year and a new Ask the Urban Dater! Today's question comes from Hakuta Bronson, a quick-oil changing technician at Spiffy Lube. Hakuta asks: My question is if a guy meets you then later keep his distant…what is he doing?...

/ January 26, 2015

Ask the Urban Dater: Shit or Get Off the Pot Edition

Alright, so here goes… a guy and myself (a girl) started off as friends with benefits. It took forever for us to actually get to the point of us hooking up, and it all started by a lot of texting. Which...

/ August 1, 2014

Ask the Urban Dater: Dating Older Women Edition

We're back with another edition of “Ask the Urban Dater,” where I attempt to give good/decent/shitty advice to random folks who read this, here, blog. Today's question comes from Arlene Jaime Lynn Sigfreud, of Grand Rapids, Michigan. She writes: I'm...

/ July 16, 2013
lonely guy

Ask the Urban Dater: What do Guys do When They’re Lonely?

Welcome to another edition of ‘Ask the Urban Dater.' Today's question comes from Heather-Jen Akins… And she simply asks: “What do guys do when they get lonely?” Hmm. I'm not sure what all other guys do; it's obviously different. Although,...

/ June 23, 2013
ask a girl out

Ask the Urban Dater: Can’t Get a Guy to Ask Me Out Edition

Sometimes these questions bug the shit out of me… I find this question a bit on the annoying side and I'm truly convinced our readers are seriously fucking with us… In any case, I'm going to serve this up and...

/ May 24, 2013

Ask the Urban Dater: The Ex That Won’t Go Away

We're at it again, more from ‘Ask the Urban Dater,' our user generated submissions to us about their problems and mishaps where we attempt to say something of meaning and use. Good fucking luck with that. So feel free to...

/ May 20, 2013