Mark is a single, gay Cuban-American living in New York—a city some say is the toughest place in America to be single. After a few false starts, he’s finally ready to go out and meet the guy of his dreams. But, first, he’d like a little bit of friendly help from Guanabee. We’ll send him to a gym, give him some style tips, get him a new outfit and turn him into Prince Charming by Valentine’s Day. So join Associate Editor Alex Alvarez as she and Guanabee help Mark get a new look, a new perspective and, hopefully, a hot new Argentine boyfriend. Because everyone could use a Marcover now and again. Your life depends on it. No pressure, though.

Mark was really impressed with last week’s advice from The Gay Shrink, so I thought it’d be nice to continue the theme of advice-giving / me having to do less work by setting up a Q & A session between Mark and the ever so sexily-reclining Gabriel. And, just as I’d hoped, Gabriel gave some really great advice. So I went ahead and ruined it all by adding my own answers as well.

Mark: So, lets see. Should I bring anything? Flowers? A gift? Too old fashioned? Or sure to melt their heart?

Gabriel: As much as I have a weak spot for romantic gestures, you shouldn’t bring gifts or flowers to your first date. Your date might be allergic to flowers, latex cock rings, or Dave Eggers. Showing up on a date is enough of a gift. Sometimes we think about the things that we would like to receive on a first date (which is influenced by old movies, telenovelas and porn) and project that onto the object of one’s potential affection. Some people don’t know how to handle gestures of generosity or affection, and might feel obligated to reciprocate against their will. If at the end of the date you feel there’s good chemistry or husband potential, you can offer to pay for the date (assuming it’s dinner or drinks or sex) with the following passive-aggressive coercive line: “I’ll pay for tonight under the condition that I see you again…” Usually works, particularly on cruise ships.

Alex: My last boyfriend brought both my mom and me a bouquet of flowers when he took me on our first date. She thought it was sweet, I thought it was sweet - and that he was a suck-up. My current dude brought me a single flower on our second date. I thought it was sweet and thoughtful and reciprocated by humping his leg in the hallway. So: Are gifts cheesy? Kind of. But I think dating and romantic things in general things are pretty cheesy anyway. So, sure, a small, relatively inexpensive gift is a nice gesture, but I wouldn’t recommend giving one on the first date. Unless things go really well. Wink, nudge, dental dam.

M: Conversation should flow normally, right? If not, Dale Carnegie has taught me to just ask people questions about themselves if all else fails, since that’s everyone’s favorite topic anyway.

G: Conversations, like gas, should flow without any obstruction. A stalling conversation might mean that there’s no chemistry, but it may also mean something else entirely. God knows I’ve been speechless on dates before. Don’t fret, it could just be that the other person is shy. A way to get your date to loosen up a bit and start talking is to pretend you’re hiring him for a job, and I’m not talking about the blowing kind. Just think of the different sections of a resume (name, address, work experience, education, hobbies) and ask him about those things. Yes, people love to talk about themselves, but make sure that your date is as interested in asking you questions as you of him.

A: Long pauses in conversation are awkward but often inevitable when meeting someone for the first time, since you don’t know what sort of common ground the two of you have. If you find yourself asking too many questions about the other person or find they’re either incredibly shy or devoid of personality, you can always comment on your surrounding environment and hope it opens the path to more conversation. Examples: “What did you think of the movie (or “film” if you’re dating a hipster)?” “This macrobiotic vegan bean curd patty is really doing my aura a lot of good. How big is your penis?” “The F train is taking forever! I think I just stepped in human feces.”

M: If its really painful, should I have an escape plan? Or should we all endure a few terrible dates to strengthen ourselves?

G: Escape plans are cop-outs invented by people with no cojones. Can you imagine Marlon Brando or James Dean pondering whether they should have an escape plan? Just be honest and respectful of the other person if you don’t think there is no potential. A simple “Thanks for your time, but I don’t think this is going to work out” and a handshake will and should suffice. Rejection is a bitch, but a bigger bitch is to make shit up to get out of a date. Remember, you’re not breaking up, you’re just being real.

A: I don’t know… I like having an escape plan, especially since I’ve been privy to some pretty horrific dates. My escape plans, however, usually amount to nothing more than fantasizing about running to freedom via a bathroom window while some guy talks about his “voice as a mumblecore auteur” over some ginseng-infused tea or other such crap. If you really don’t want to wait out the remainder of a painful date, just say you feel like you’re going to vomit or that your crabs are itchy. Diarrhea is always a good excuse to leave, as well. Plus it totally embarrasses the guy you’re with when the waiter has to come by and mop it up, almost ensuring he will not call you for a second date.

M: If it goes really well, do I just play it by ear? Is there such a thing as too fast? Or is it just as long as I’m comfortable. What about keeping them wanting more - how do I guarantee that date one I really enjoyed leads to date two?

G: Somewhere between “The Dating Game” and “Sex in the City” we have forgotten the fact that dates are nothing more than a fun, improvisational way to meet another human being. If you’re both into each other, it won’t matter if you’re watching hiptards go by. Going too fast, or not fast enough is entirely relative, and a function of how you feel about each other. I know couples who have been together for over 10 years after meeting once in a bar and almost immediately moving in with each other.

As for securing a second date, just be honest without being too pushy. If you’re having a blast and the other person is not, just accept it without taking it personally.

A: If you feel there’s enough chemistry and/or witty repartée between you and your date, definitely give him a call or IM or Facebook SuperPoke (That’s sarcasm. Please don’t ever use this feature.) and ask to hang out again. As for asking “too soon” and looking desperate, well. It’s only desperate if he doesn’t feel the same way, isn’t it?

M: If I’m not into it, but they are, how do I kindly turn down date 2? I’m a nice guy after all and just not answering phone calls or text messages isn’t my style.

G: Again, honesty goes far, and earns you lots of karma points. Be nice and respectful when rejecting other people, because you don’t want drama, a restraining order, or a pig’s heart stabbed to your door. Tell/email/TXT the other person that you don’t feel things are going to work out, kthxbye.

A: Pretend you’ve died.

M: Anything else I should be super aware of as I enter this gay dating scene? Tell me everything you would want to know.

G: Dating requires a lot of mental agility, because one has to concentrate on oneself as much as the other person: Do I have foie gras on my nose? Is he really wearing Jordache jeans? Also, let’s face it, men are pigs and gay men are no exception. Nonetheless, keep in mind that dating should be a non-traumatic experience, and one that requires patience and practice. Above all, before feeling comfortable on a date, you need to be comfortable with yourself. If you think you deserve greatness, you won’t settle for less. And above all, always wear a condom.

A: Dating should be fun. It often isn’t but, Christ, it should be. I find alcohol helps. But, although it does lower my inhibition and mask my out of control awkwardness, it can also lead to my doing and saying embarrassing or irresponsible things, like vomiting or making out with an ugly person. At the same time. Or performing karaoke.

So, you know. Take it easy on the Pretty in Pinks or whatever it is you’re drinking these days, Mark.

And remember: You’re awesome. And whether or not whoever your date is recognizes it, you will remain awesome.