The Gay Date

So the cute guy from the bar/gym/Starbucks/car wash has given you his phone number. Now comes the tricky part, how to negotiate the first date without making yourself look too needy or easy which of course you are, but you don’t want to appear that way. Here are some dating tips I have learned in the over 20 years I’ve been out and dating guys.

Who should call whom? I’ve found in my own dating experience that I usually have to be the one to call. I used to think it was because I was such a strong personality I intimidated guys. Now I just think it’s because most guys are just as scared as I am about making the first call. If I am interested in someone I need to make the first move. Definitely if you ask for their phone number you should be the one to call. But if you wait for someone to call you for a date you may be sitting at home surfing adam4adam all night. Don’t text…it’s too impersonal. Also, learn how to take “No” for an answer because if you’re putting yourself out in the dating world, you’re going to hear no a lot. One of the most difficult things I had to learn was that when someone said they didn’t want to go out with me it didn’t have anything to do with me. Maybe they’re attracted to young, slim Asian guys, something I will never be no matter how many salads I eat. Unless you want to become a stalker, let it go. A guy saying no is not the end of the world but a restraining order could be.

If he says yes, then the next step is the date itself. I like Thursday night, the official Gay Date Night, for a first date. It’s perfect. Thursday is close enough to the weekend that you’re a little excited about tomorrow being Friday, yet it’s not actually the weekend so if the date bombs you haven’t actually wasted a weekend night on him. If the date goes really good you have enough time to plan on a Saturday or Sunday date without seeming too easy. Plus you have all day Friday to sext him and flirt before the weekend.

Spank the monkey before you go. It’s not just a laugh line from “Something About Mary” it actually is a good idea. You can focus on him instead of worrying about whether you’re going to get some after dessert. If you’re like me and have a time of the month when you’re especially randy, you may want to clean the pipes twice that day, once in the morning and then just before the date. Just be sure to do it before you shower so you can make sure you’re tidy before the date.

I’m not a big fan of the Movie date, unless it’s in conjunction with a dinner. You can’t get to know anyone sitting next to them in a movie theatre. A coffee date is good if you’re really not sure you want to commit to the full on dining experience. Plus you can tell a lot about a guy by what he orders at Starbucks.

If I call and ask him out I always plan on paying for the dinner. There are lots of great places in Oak Lawn where you can take a date on a budget. The Bronx is a charming, romantic place that’s not too expensive. One of my favorite places is Green Papaya because most of their entrees are less than $10, and it’s sort of sexy sharing a shrimp spring roll with someone and letting them dip in your peanut sauce. Parigi, the Oak Lawn Country Club, is another good place. If you don’t think you can afford dinner, meet for Sunday Brunch. The most important thing is to keep it casual ( read- inexpensive). I took a guy I was really crushing on to Star Canyon once back in the day, we had a wonderful dinner, shared a piece Heaven and Hell Cake, and I thought I was all set to share another piece with him…then when I took him home his next date was outside waiting for him. $100 bucks down the drain on a total loser.

If you drink, don’t drink too much. It might seem like fun to share a bottle of wine with someone, but if you’re going down that road you run the risk of becoming a sloppy drunk and unless the guy you’re dating is a sloppy drunk too, it’s not attractive. If you are both big ol lushes, then you have more serious problems than working on your dating skills. If you don’t get help at Charter get help somewhere.

Don’t, under any circumstances, flirt with the waiter. You may have decided by the time the tea arrives that this guy isn’t for you. That’s fine, but don’t humiliate him. I had dinner with this douche at the Bronx one time, it was clear to me (and obviously to him) that there wasn’t a connection, but he proceeded to flirt shamelessly with the waiter through the whole dinner. As I left I saw him slip his number to the waiter. Seriously? You don’t want to put that sort of dating karma out there in the universe.

Don’t dominate the conversation. You may be the most charming and interesting person in the world, but if you are believe me it will come out naturally without you having to sell yourself like a tranny hooker at the Diamond Shamrock. Usually guys make this mistake because, (A) they are nervous or (B) they are really self-centered. If the guy you’re sitting across the table from is talking about himself nonstop, try to put him at ease…if that doesn’t work then he must be a douche and you can delete his number from your Blackberry when the date is over. If you’re nervous, try to remember that this Chinese dinner is not the most important dinner of your life. It’s just a date. Dating is what we do to learn whether we like someone, to separate the gay wheat from the chaff. I like the Wikipedia definition of dating as “a form of courtship and may include any social activity undertaken by, typically, two persons with the aim of each assessing the other’s suitability as a partner.”

Ask him questions about himself. Most people love to talk about their lives. But be sure to notice if he asks you about your life. If he doesn’t then he’s probably too selfish to date. Don’t ask him about past relationships because it doesn’t really matter what he’s done in the past and most guys don’t like to hear the “relationship” word in any form on a first date. There will be plenty of time for that. If he talks incessantly about his ex boyfriend then he’s probably not available to date you because he’s still in that relationship. There are certain questions I will artfully dodge on the first date. How much money I make is one, who my friends are is another (yes, I had a guy ask me that one time only to name drop the rest of dinner). Those two questions are big warning signs that you have either a $40,000 millionaire or a social climber on your hands…and unless you’re into that type don’t answer natch. Luckily I’m really good at small talk so this part is easy for me, but some people find it difficult. Find out what he’s interested in and talk to him about that. Silence is okay as long as you’re staring into each other’s eyes longingly.

So you’ve made it through dinner. If you’re both into each other then maybe go for coffee or a movie if he’s up for it. Try to avoid going to a club on the first date. Clubs exist for two reasons, for people to get drunk and to find tricks. If you positively have to go to the club, drop him off and say good night and go about your merry way. I’m not the arbiter of anyone’s sex life so I can’t tell you whether to give it up on the first date. But waiting a little for the big event can make it more exciting when it actually happens.

I no longer believe in love at first sight, although I do believe that we are attracted to certain people initially but we shouldn’t overlook people we don’t feel an instant connection with. That guy who keeps chatting you up at the gym that isn’t perhaps an Adonis may be total husband material, but you’ll never know unless you give him a chance. Dating helps you figure out if that spark can kindle itself into a fire. But if you put too much weight on the first date you will come off as needy, grasping and desperate. You may be all three of those things but you don’t want him to know that right up front. Let them fall in love with you then you can each unpack your bags of neuroses together.

Have fun and Happy Dating!


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