Dating Do's And Don'ts

10 Rules For Asking Out A Man On The First Date In The Age Of Grindr

By · 24 comments · Updated on January 27, 2016

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Screen Shot 2016-01-18 at 12.57.45 PMNow that marriage equality is the law of the land, it is time for our community to learn how to date properly.

Two guys interested in each other romantically can stumble over those initial bumps in the road to romance and even marriage. Who asks who what, and when? With so many definitions of what makes a relationship, with open debate on the importance of legalized marriage or whether or not to be monogamous, it can be overwhelming to even think of how to ask someone out on a simple, old-fashioned date. And despite the prevalence of so many ways to find sex online, there are still a lot of us who prefer the good ol’ dinner and a movie.

We certainly don’t know the secrets to living happily ever after, but we do have some pointers for how to at least properly meet someone. Hint: good manners are always a good idea.

1. If you want to go on a date with him, ask him out

Welcome to the 21st Century, when straight women are empowered enough to ask men out. That means no one, gay or straight, should wait around to be asked. Perhaps you are shy, and that is a challenge, but everyone is scared of rejection. In fact, is selfish to expect someone else to always take the risk. And telling him, “Here is my number, text me if you want to go out sometime” is so depressingly passive, it does not deserve him giving you a response. Don’t be a wimp.

2. If you take the initiative to ask him out, have a plan of what you want to do

It was your idea to ask, so you should actually have an idea of a place to go. Asking him to go out, and then following it with the question “So where do you want to go?” or “When?” is the worst. He may not have been thinking about going out with you, and suddenly placing the responsibility on him to come up with a plan is stressful and rude. If you can’t think of someplace to go, it suggests that perhaps you are, sorry to say, boring.

3. If you offer the vague, non-committal “Let’s go out sometime,” and he agrees, you have three more texting encounters to finally make a suggestion

Asking someone to get together “sometime,” but never finding the time to do it, means you are always finding other activities you would rather do than go out with him on that date you suggested. So hurry up and make a commitment.

4. If you ask him and he declines, you can certainly try again (and you should, life is short), but it is his turn to ask you

Perhaps he doesn’t want to, which is a bummer but life goes on. Or, perhaps your first invitation was very casual, so ask a second time with a more specific suggestion. At least you tried. If he wants to pursue any sort of connection—on a date, as friends, whatever—he needs to meet you halfway. Never chase anyone. Sadly, there are people in this world who will keep sending you “What’s up” text messages only because they seek attention more than they seek affection.

5. If you asked him out, he said yes, and you agreed on a day/night of the week, always have a plan set before you go to bed the night before

Even if it is a quick message of “I get off at work around ____, I will text you then,” that is enough to let him know you remembered, and you respect the fact that he can’t wait around for you all day. And for God’s sake, remember Rule #2. Be a man.

6. strong>If he asks you out and you want to meet, but you already have plans for the time he suggests, then offer another time.

Suggest something immediately, during that conversation. “I am busy on Friday. How about Saturday?” Boom. Done. If you aren’t sure of your schedule, of course you have the right to take a day or two to get back to him. But if you turn him down, and then a week or two later you text him, “I’m not busy now!”…good for you. His invitation has expired. You are not living in a Tennessee Williams drama, a southern belle sitting on your porch, sipping tea and welcoming gentlemen callers to woo you into marriage. You made him wait, so take off your hoop skirt. It is your turn to ask.

7. Stop sending countless texts and “smiles” and “woofs” on hookup sites to young, complimenting them simply for being young and beautiful

Carrie Fisher wisely said, “Youth and beauty are not accomplishments,” and she perfectly summed up the crisis that has engulfed our community’s next generation. In years past, young gay men (and all youth in the LGBT community) suffered without a support system to guide them as they learned how to become adults. When once we treated them with indifference, we now threaten them with overindulgence, as it is so easy to endlessly compliment them for doing nothing other than taking a selfie. Sending a 21-year-old a “smile” on Adam4Adam or a “woof” on Scruff is nothing more than a fleeting thought, an effortless gesture; but those messages add up in their inboxes, and eventually those lovely young men think they somehow deserve the attention provided by the lists of men who apparently think they are special. These boys have learned to view the outside world from the perspective of their identities as sexual objects, and when someone innocently attempts to speak to them as actual adult humans, it is presumably yet another tiresome attempt to have sex. Or, they become offended when they realize it isn’t. Either way, no one wins. Save your compliments for the people, young or old, who you actually know and like. Compliments should be part of an actual conversation.

8. An introductory phone conversation can tell you a lot about him, in just minutes. 

Cell phone technology has ruined the experience of talking on the phone, with garbled voices and never finding a convenient moment for both persons to talk. Endless texting, with the “What’s up” and “What do you like to do for fun” and “What are you into” questions, is no way to get to know a person. Speaking requires you to contribute to the conversation. So talk on the phone at least once, just for a few minutes, before you meet. Schedule a time, turn off your TV, sign out of Facebook, turn on some background music, and chat about your day. If you need something to do while you talk, fold some laundry or something similarly mindless. Then say “Thank you,” make a plan to go on a date (or don’t), and hang up and go on with your life. Meeting for the first time and being confronted with what he really looks like and acts like AND sounds like can be unnecessarily awkward. FYI, simply listening to a texted recording of his voice doesn’t count.

9. Sending a text message in front of someone else is the same as having a secret conversation

Imagine you are on a date. Someone walks up to your companion, they whisper something to each other, and they don’t tell you what they just talked about. Strange, yes? This is no different than being with someone while texting someone else. Texting has become a social necessity, but your date has no idea if you are sending a message of “This guy is so ugly and boring” and you are planning an escape. Or perhaps he thinks you just got a message on Grindr, and you’re texting back that you are on a date but can meet up for sex later. Even if it is an innocent message to your co-worker, isn’t your date important enough to put your phone away and pay attention for an hour? If it isn’t, perhaps you should leave and stop wasting his time. But remember: if you are always looking for something better, nothing will ever be good enough.

10. Whoever asked to go on the date, pays for the date

Asking a guy to meet you for a cup of coffee may not seem like a big deal, but still, buy him his stupid cup of coffee. In a perfect world, with two adults who both have jobs, you would each pay for yourself all the time. But even the most expensive cup of coffee is only $6, so show a little panache and thank him for taking the time to meet you in person. If you ask him to an expensive restaurant for dinner, don’t expect him to pay for his half. He may not be able to afford it.

Do you have suggestions for how to treat a guy on his first date?