friendship

Supporting What Doesn’t Make Sense!

Dear T,

My best friend has been in a relationship with this guy for about 6 months now, and I can’t stand him.  For the life of me, I cannot understand why they are still together.  There are plenty of reasons for my friend to dump this guy.  For starters, this guy claims to be in between jobs, and has been taking money from my friend for a month.  Then there is the fact that the guy constantly talks to my friend about being too feminine.  When I’m around them both, my friend tries to butch up and be something he’s not.  And to top it all off, dude has cheated on my friend.  I keep telling my friend to dump his ass, but he can’t let him go.  How long am I expected to tolerate this man and not cuss him out?  I appreciate the advice.

Thanks,

Angry Woe

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

The Lifestyle

Top or Bottom, How Do You Know?

Dear T,

I’m new to this whole gay thing, and kind of confused.  I’ve been doing research, so I know the difference between a top and bottom, but not sure how to tell one from the other.  My instinct tells me if a guy acts like a guy and likes guy things, then he’s a top.  And if a guy acts like a girl and likes girly things, he’s a bottom.  However, the more dates I go on, and the more I’m around gays, the more I realize my instinct is wrong.  Can you tell me how you can tell the difference?

Sincerely,

Baby Gay11

relationships

Before You Tell Him “To the Left, To the Left.”

Dear T,

Would you stay with someone if they cheated on you?  I’ve been with this man for 2 years, and last week he told me while he was at this house party with his boys, he let some little young THOT suck his peen.  When I asked him how could he do that, he copped out and blamed it on the liquor and peer pressure.  No lie, a grown ass man gave me the peer pressure excuse.  However, I will say he seemed genuinely sorry and reassured me he would never do this to me again.  I told my friends what happened, and they all told me to dump him.  I just don’t know if I want to do that, because I still really love him.  So please, hook me up with some advice.

Thanks a bunch,

John Doe13

friendship, relationships

“What About Your Friends……”

Dear T,

I have this best friend and we’ve just not been clicking lately.  I’ve been with my current boyfriend for about 8 months, and ever since then my best friend has been distant.  We don’t talk as often, and I can count on one hand the number of times I’ve seen him lately.  And before you think it, I’m not one of those people that get lost in a relationship and completely forget about his friends. My other friendships are just fine.  I talk to my other friends nearly all the time.  I thought maybe my best friend had some issue with my boyfriend, but my bff claims to like him.  Plus, my boyfriend is the nicest guy and gets along with everyone.  What do you think the problem is?  What should I do to get my friend back?

Sincerely,

Mysterious Gay

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

The Lifestyle

I Say, Come On Out that Closet!

Dear T,

I’ll just get right to the point.  I’m 25 years old, a black man, and gay.  The problem is, I haven’t “come out” to my family yet.  My mom and dad are very old school Christian, and my two older brothers are kind of homophobic.  I’m afraid that if I tell them I’m gay, they won’t talk to me anymore.  On the other hand, I’m tired of living this secret double life.  I know people say I have to live my truth, but I don’t want to lose my family while doing it.  They mean everything to me.  What do you think I should do?

Thanks in advance,

Still in the Closet

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