Dating

That First Time!!!

Hi T,

I heard about your blog from Instagram, and decided to hit you up since you keep things anonymous and all.  I’m not really out the closet or whatever yet, and don’t have friends I can ask about this whole gay lifestyle, so I’m coming to you.  Here’s the thing.  I’ve never had sex with a man.  I’ve always wanted to, but never did because I knew what that would mean.  But now since I have started to accept that I like men, I think I’m ready.  I started messaging back and forth with this guy I met on one of these apps, and we’ve been talking about meeting up.  Crazy thing is, I’m really nervous.  I probably shouldn’t be because I’ve had sex with girls, but I am.  So do you have any advice for a virgin gay?  I mean what was your first time like?

From,

Gay Cherry Poppin

Dating, relationships, The Lifestyle

Is 30 too Old for a Midlife Crisis?

Dear T,

I’m not really seeking advice about dating or relationships, but you did say people can ask you anything, so I’m asking.  I kind of feel like I’m failing in life.  I had always envisioned that by the time I was 30, I would be in a career I loved, with a man that adored me, and in a nice house with a dog.  Unfortunately, I’m 28 going on 29, and I’m not even close to achieving any of this.  I’m up to my neck in student loans, can’t find a GOOD man anywhere, and I’m stuck in a job I hate that’s going nowhere.  Don’t get me wrong, I’m grateful for what I do have; but I’d be lying if I said I wasn’t a little disappointed.  I guess my question is, do you think I should feel like a failure?  I hoping you can help.

Thankfully,

Almost 30

Dating

Confidence is Sexy!

Hey T,

I’m going to try and keep this brief. Since social media has become such a big thing now, I’ve become increasingly more insecure. Men are posting pics of themselves with their rippling abs, their superman chests, their Hulk like arms, and their huge legs and butts that can crack walnuts. And then I look at me. Standing at 6’2″, weighing 240, with a medium/large build, a keg for a stomach, and a butt barely visible. Thankfully I’ve been told I have a nice smile and dimples. But honestly, how is a guy like me supposed to catch someone with mini versions of Captain America and the Black Panther walking around out here?

Sincerely,

D.C. Marvelous

Dating

Dating Outside of Your Race is OK People!!!!!

Dear T,

I’m on the fence about dating this guy I met, and I’m hoping you can help me out a bit.  He seems like a good guy. He has a great job, is very funny, his smile is sexy, and surprisingly he has an amazing ass. However, he’s white and I’m black. And please don’t think I’m a racist or something. It’s just that when I envisioned my boo, it was a man of color. I can’t imagine bringing a white man around my friends, or taking one home to meet my mom. Plus, we come from different cultures. I’m not sure if I’m talking myself out of something that I don’t need to or what. That’s where your advice comes in. Thanks in advance for help.

Sincerely,

GuessWho

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