Dating

I Ain’t Saying You a Gold Digger, But Are You Messing with Broke…?

Dear T,

I have a quick question.  What classifies someone as a gold digger?  My friends call me that from time to time because I won’t date anyone that doesn’t have a certain amount of coin.  However, I don’t think that makes me a gold digger.  I think that just makes me a guy that has standards.  But what do you think?

Sincerely,

Off The Runway89

Dating, The Lifestyle

“Yo, Let Me See Your Booty!”

Dear T,

Can you please tell me why sending nudes or partial nudes seems like a must now a days in dating? I’ve tried pursuing things with a couple of guys over the past few months, and a few days into texting back and forth with each of them, they want me to send nude body shots of myself. Are naked selfies just an expectation of building a relationship now?

Sincerely,

Chi Town’s Finest

Dating

“Age Ain’t Nothing but a Number” Or is it?

Dear T,

How old is too old for me to be dating?  I’m 23, and I started dating this man I met at a bar who is 44.  My older sister told me I have no business seeing him because he’s too old, but I like him.  He’s well groomed, has a good job, and makes me laugh.  And he’s so much more mature then the guys my age.  What do you think?

From,

Young But Ready

Dating

This Man Is Not Yours to Have

 Dear T,

I’ve been seeing this man for about 3 months now.  He’s everything I’ve wanted.  He’s cute, has banging body, has a great job, makes me laugh, and the sex with him on a scale from 1 to 10 is an 11.  The only thing is, the guy is married and has no plans in the near future to get a divorce from his wife.  He told me he didn’t want to get a divorce right now because he didn’t want to do that to his two young kids.  However, he always makes himself available to me.  We don’t really go on dates around town, but he comes over to my place often and takes me on trips.  Lately though, I’ve just been feeling our relationship the way it is, isn’t enough.  I want more.  I want to go out in public on dates. I want to be able take pictures with my boyfriend.  I want to roll over in the middle of the night to him sleeping peacefully, instead of him making a mad dash for the exit to get home.  Plus, I’m starting to feel bad for his wife.  I guess I’m writing to ask what do you think I should do?  I’ve asked my friends, but I don’t think they get it.

From,

Oliver Pope

Dating

Where’s My Man and Happily Ever After?

Dear T,

I don’t know what it is, but I can’t find a man.  I haven’t been in a relationship going on 4 years now.  Don’t get me wrong, I’ve been on dates since my last relationship. But the guys I’ve gone on dates with wound up being a quick fling, or a complete waste of time.  And I’ve tried meeting guys everywhere.  I’ve tried bars, clubs, house parties, and even created profiles on stuff like Grindr, A4A, and Jack’d.  I’m not sure what I’m doing wrong, but do you think you could give me some tips on how to land a boo?

From,

I’m Fine Alone, But Damn

Dating, relationships, The Lifestyle

I’m A Top, You’re a Top! Let’s Make it Work!

Dear T,

So I really like this guy that I’ve been dating for the past month.  We have amazing times together, can talk on the phone for hours, and have a ton in common.  Plus, he has a great job and is fine as sh$t.  Surprisingly, we haven’t had sex yet.  Which leads me to my problem.   He’s a top and he’s under the impression I’m a bottom, or at least verse.  I’ve only bottomed once, and I hated it.  Like I said, I’m really feeling this guy and I’m afraid if he finds out I’m a top too, he’ll drop me.  What do you think I should do?

Thanks in advance,

Hole But No Entry

Dating, relationships

Can a Old Flame Be My New One?

Dear According to T,

I’m on Round 2 with this guy. We dated a few years ago, but are exploring things again. Last time, he bailed. This time, I want to. Not to “get him back”, but because I feel he is too emotionally stretched to fully engage…especially sexually. I am wrong for wanting to call it quits?

Thanks,

Hates.Recycling

Dating

Watch Your Mouth

Dear T,

So I’ve been talking to this guy for about three weeks and he won’t kiss me on the lips.  However, he doesn’t mind my lips in other places if you know what I mean.  What do you think is up with this guy?

From,

No Kisses.