Ask the Urban Dater: Pity City

the Urban Dater is back with another addition of ‘Ask the Urban Dater,' where you guys get to ask me a fucked up question and I give you an equally fucked up, or shittier, answer.

Today's question comes from an NYC socialite by the name of Stromhilda Viceroy Olmreaugarde, who manages a sticker store on w 23rd and 18th. She reminds you to say it with a smile… and a sticker. Whatever the fuck that means. Alrighty then, let's get to it!

There was a guy I had been messaging with back in November in hopes to help me move on from my ex. He would message me all the time and never ask me out. Finally before the holidays he did try to make plans. Alas, I was super busy getting ready to go Rotterdam. So now I'm back and he's been messaging all the while. This has been going on for so long that I've sort of lost interest and to tell you the truth I might need a little break from men. But, I feel like he's asked me out so many times that I should at least go on one date. So I'm going out with him tomorrow night. How do I change my attitude about this? I'm not the type of person to show up and not have fun or act like a bitch. But I'm not really looking forward to it and that makes me feel guilty. Ever felt like this? – Stromhilda Viceroy Olmreaugarde

Just a thought, but it almost sounds like you're going out with this fella cause you feel sorry for him. Perhaps. I mean, if you're going out with him because he's persistent. That's a different story. But I'm reading this like you just don't care all that much and you're like “fuck it,” he asked, so I'll go. It's the least I could do

I mean, I wouldn't want to go out with a girl that felt sorry for me… Not even when I was going through my “sexual drought.” Okay, that's a lie. I totes would have.

It's hard to snap out of that funk… Maybe you do need a break from the fellas… Maybe. I tend to think you just need a break from the wrong fellas. It sounds to me that even though Holmes boy took a while to ask you out, he did reveal himself through his actions… I always say that actions tell the truth, so pay attention. If a person's actions work to bring you together then that means something.

That said, I say go out with him. Don't put pressure on yourself and remember, there shouldn't be an expectations here. Just two cool people going out for a drink, a bite and some good times. If you can manage that, the rest will work itself out just fine, dear. True fact.