Dating, friendship

Breaking out of “The Friend Zone”

Hi T,

I have a question for you.  Is it really impossible to get out of the friend zone?  I have this good friend that I’ve been cool with for about 4 years, and I want more than friendship.  When he and I first met, it was at a mutual friend’s birthday party.  I remember initially thinking at that party how sexy he was, and that I wanted to sleep with him bad.  However, we wound up just talking that night and built a really great platonic relationship.  Since then, we’ve been in the friend zone.  And it’s not like I’ve been pining away for him for four years or anything.  I’ve dated other guys, but it’s never worked out with any of them.  He on the other hand, has been in a relationship with some dude for 2 years.  Although, word on the street is his boyfriend has been cheating on him.  I guess that’s beside the point.  Anyway, do you think I should risk our friendship and tell my friend how I feel about him?  I was actually thinking of a plan to tell him about his boyfriend sleeping around on him, comfort him for a week or two, then make my move.  I appreciate the help.

Thankfully,

Gay Cleveland Brown.

Dating

Dating Daddy Daycare

Dear T,

How do you feel about dating a guy with two kids? I’ve met this great guy and we’ve been really vibing over the past 2 weeks or so. However, we haven’t been on a date yet because his schedule has been super busy lately. He said his one kid has been sick, and the other one has been having issues at school. And there in lies the problem I guess. I’m nervous that if I start dating this guy and we try to build something, it wouldn’t work because he won’t have time for me. Am I making this a bigger deal than it has to be? Should I just go out with him?

Much appreciation,

No Baby Daddy

Dating

Finding A Boo at the Workhouse! Good Idea or Recipe for Disaster?

Dear T,

So I’m really feeling this guy I work with.  He just started working in my office about 3 weeks ago, and since then we’ve just clicked.  We have a ton in common and I can just tell there is crazy sexual chemistry between us.  Honestly, I sometimes get horny sitting at my desk thinking about him.  However, my cousin told me not to get involved with the guy because we work together.  I get what he’s saying, but I really want to pursue something with this guy.  Appreciate the help, and really like what you have going on here with this blog thing.

Thankfully,

Bad Romance

Dating, relationships, The Lifestyle

Be a Top’s kind of Bottom, and A Bottom’s Kind of Top.

Dear T,

I’m just starting to try this whole gay thing out, and I was wondering if you could offer me some tips.  I’ve been in a two month long relationship, and have yet to have sex.  As I prepare to take that step with my boyfriend, I’m seeking some advice.  Like what advice would you offer to someone that wants to be a great bottom?  And actually, what advice would you offer to someone that wants to be a great top?  I think I have an interest in being versatile.

Thanks for the help,

Gay Virgin96

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