How My Gay Best Friend Helped My Dating Game


Fellas, have you ever been on a date and started thinking, “Man, it sure is hot in here.” Well, you know where that heat is coming from, you. You’re sitting in your best shirt and slacks, staring at this attractive woman, finishing off a magical date night and yet you’re still very nervous. You’ve most likely sweat so much that the boat shoes on your feet would be officially capsized. Anxiety is catching up to you and before you know it, it’s day three and she hasn’t even read your goodnight text. Where did you go wrong, how did you come up short, what wasn’t good enough?

These were questions that I would often ask myself when I found myself in similar predicaments. But, the answers that would be given could never satisfy what I felt inside had become some personal indignation towards the opposite sex. Therefore, the advice procured from my female best friends felt like secret Intel from double agents, with me having no way of knowing if they were really on my side. Then one day I came to the realization that it wasn’t the information I was getting, but who was relaying it to me.




This is where my brilliant idea came in; instead of having females give me the what’s what about the opposite sex, why not have a guy do it? “Well that’s because guys don’t know what they’re talking about,” this is true Sharon, now please sit down and let me finish. Heterosexual men don’t really know what goes on in a woman’s mind because frankly, they don’t spend enough time trying. To give legitimate, valuable information on anything, especially females, as a man you would have to be around them almost exclusively, able to access information normally closed off to the general populace, infiltrate their most secret and sacred sanctuaries, and most importantly, look at men the same way they do. The conclusion that I came to was shocking: I need a gay best friend.

Now I myself am by no means attracted to males in any way, shape, or form, but I can appreciate the pursuit of affection that every person embarks on throughout their lifetime, regardless of sexual orientation. Being the eclectic that I am, any gay male would not suffice. I need this potential confidant to fit my personality, and I have found the best way to do this is by putting them in front of a camera and asking them charged personal questions. Fun right?  To cut this long foreword short, I met a man named Rolando through my other close friends, and these are my interactions with him during the pursuit of My Gay Best Friend.

Rolando, I’ve covered the basics with you. Why do you think you would make a viable Gay Best Friend for me?

Well, I feel that you take what you do seriously, and I admire that. Even though the subject matter may be a bit facetious, if properly executed I think this could blossom into something great.

Facetious, nice SAT word.

Hun, we’re both a little old to be talking SAT’s, okay?

Touché. Let’s do a quick trial of how I picture this segment going.

Let’s do it.

Hey Ro, I went on a date with a chick a few days ago, and she still hasn’t messaged or called me back. Did I mess up somewhere, and if she doesn’t tell me, how am I going to fix it for the next time?

What did you wear?




What? Why does that matter?

Because presentation is key, girls like men who look like money. Now I’m not saying that you have to HAVE money, you just have to look the part. That first impression gives them a sense of your taste, your style, your swag. She’ll pick out a bargain-bin shopper in 2.2 seconds. You have to be able to match her fly, whatever level of bird she may be.

Okay, I get that. She wasn’t really the “superficial” type, though. In fact, she was basically a hippie. We went to a hookah bar and she had her own mouthpiece in her bag. So I don’t know if my dress was that big of a determinant.

Style is ALWAYS a factor, whether you have it or not. What do you think is keeping her from sending you that little heart eyes emoji,  then?

I honestly don’t know. I did everything I was supposed to do. I paid, I held doors, I even complimented her eyebrows. What else is there?

That was funny, you’re funny. Did you make her laugh?

Of course I did. She laughed all night.

Yes, but did she laugh, or giggle?

What’s the difference?

Giggles were made specifically for flirting. Girls can still look cute when they giggle. Now a laugh is something that you have to cross a certain threshold of comfort to do. Some girls snort, some make ugly faces, some may sound like hyenas. If you had her laughing all night, that might mean that she may not take you seriously as a partner, and you just placed yourself in friend-zone territory.

Wow, do you really think that’s why?

Maybe, What happened at the end of the night?




I dropped her home; we sat and talked for a little bit. Then I walked her to her building, we hugged and said goodnight. That’s it.

Was it a church hug?

What’s a church hug?

Two arms, a lot of space in between the stomach’s and chests. Jesus should be able to walk through there.

Oh. Yeah, that was kind of how we did it.

Were her arms above, or below yours?

Below . . .

Congratulations, you just made it into the Friend Zone. Your benefits package includes; late night talks about why “He” is such a jerk, invites to happy hour, and being shouted out on various forms of Social Media. Don’t forget to make sure her hair stays out of the toilet on the nights she has one too many.

[Laughs] All right, I get it. Cool, that was great, I loved it. I think you just may be the guy for the job.

That was the gist of the conversation, Rolando turned out to be really witty and humorous. Together, we will put out our “My Gay Best Friend” series and try to answer the world’s most provocative questions. I look forward to hearing what they are. Be sure to leave your suggestions down below!

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