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

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

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, 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

friendship, The Lifestyle

His Business, Is Not Your Business

Dear T,

I have this female best friend, and over the past three months she has developed a huge crush on this guy we know.  He’s fine, a recent college grad, and charming.  I think he’s a good catch, but I’m pretty sure he’s gay.

Shortly after meeting this guy, my best friend and I became Facebook friends with him.  Since then, he’s been messaging me directly pretty regularly.  We talk about our life goals, our experiences in college, sports, and other things.  While that sounds normal, when we have our Facebook chats it’s usually after 11:00pm.  Also, he uses smiley wink faces in our conversations.  And looking at his Facebook profile, I learned he loves Oprah and Rhianna, and we have multiple friends in common that I know for sure are gay.  So I guess my question here, is do I tell my best friend this guy is gay so she can move on?  Or do I keep the information to myself?

Sincerely,

Trying This Out