Dating Do's And Don'ts

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



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?

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  • Anthony Dilsaver

    I messaged him on Grindr and said “hey slut come over and I’ll make u pizza” been together ever since

  • Leo J Dineros

    Yup. I asked mine to meet me halfway and now we’ve been together almost 4 year’s.

  • Jaden Birns

    Thanks for these dating tips for the modern gay guy in the age of Grindr.

  • Realitycheck

    LOL You like him, he wants you….open your modern LOL gay Grinder mouth and say…… lets go out! Done….

  • Glücklich

    Hmmm…y’know, it’s not like I’m SOOO old but I can’t imagine trying to set up an actual date-date through an app.

    My experience has been a little flirtation, a few well-placed compliments on something other than appearance, and leveraging at least a couple shared interests works wonders.

    And give a little chase. Men like to feel desired and some, like me, enjoy working for it.

    Also, I’m all for sexual freedom but there is something to be said for delayed gratification. My most gratifying experience was the culmination of a six-month flirtation and string of dates. That the situation was challenged by workplace dynamics added to the pleasure I derived from…not wooing…but working to seal the deal. The attraction was mutual and obvious but neither of us spoke of it FOR MONTHS and then…fireworks!

  • sprocket

    So many of these are common sense. But after trying Grindr, I realized it’s neither common nor sense. If Grindr achieved anything, it was underscoring the imperative to get out and meet people in person.

  • Maude

    “Youth and beauty are not accomplishments.”

    Boy, is that ever true. I’ve met and bedded some very good looking men but found a few of them not to have a brain behind the handsome face, and in-shape body.

    They are good at pick-up ‘casual-speak’, but after that, not a clue.

  • batesnight

    Great article and so true. Was suspicious at first if this was going to be another backwards viewing dating article and realized the writer nailed it at every turn. Except for the part about using Grindr as a dating app. It’s a hook up app, so let’s face that reality. Sure there are some who have met on there and had a committed monogamous relationship that has stood the test of time, but I’ve never met that couple. I’ve only encountered the opposite. The perpetual single living on grindr.

  • 1898

    All of these suggestions seem like common sense to me, but sadly the guys I’ve interacted with on grindr and scruff are so socially stunted that they’re barely able to put more than two words together in a sentence, much less have a conversation and make a plan.

    This article should be required reading.

  • SEAQueer

    Roses are red / Gender is performative / Mass-market romance / Is heteronormative

  • ibernard

    So what do you do when your friends have been dead for about 26 years? You’re in your 50s, either look it or don’t, and really don’t do bars? Those in their 20s, 30s, maybe 40s, still think 50 is dead. If you took care of yourself throughout the AIDS crisis, and find yourself in a string of situations with guys who have ABSOLUTELY NO CLUE AT WHAT WE WENT THROUGH, your work is ahead of you, and it’ll take an intelligent and polite guy to recognize that life isn’t PrEP and TRUVADA and having an account on every hook-up site.

    I say bring back the disco ball. And a little flirtation between songs.

    Well-written article. Definitely required reading.

  • martinbakman

    At first I didn’t agree when the article said how marriage equality makes dating skills more important than before.
    But if marriage is your eventual goal, then yes, dating skills can be critical.
    One can look at dating as a way to screen out guys that are not up to par, sort of an interview process, so that you’ll be spending more energy around decent men, on our path to those wedding bells.
    My honey and I met through mutual friends, which is a common way couples meet. So make sure to maintain your social network of friends even while you’re being a slut in the age of Grindr. :-)

  • EvonCook

    Well, as many have already said, most of what you suggest is common sense, good manners and etiquette, not to mention respectful of other human beings that might add to your life as friends and become chosen family. However, I certainly hope a simplistic and totally un-gay direction of the article is not to turn the gay community and younger, impressionable minds into little faux heterosexuals or valley girls desperate for a husband, destined for the suburbs with their romantically perfect soulmate and the complete answer to all their dreams (certainly a lesbian ideal: the wife, the house, the sofa)–since that would totally surrender our most special, subversive qualities, assimilate gay progress into oblivion and give up the very nature of being gay, homosexual, queer, to be just another one of the pathetic, shallow, and primarily empty commercial prospects for a greedy, religionist, capitalist society to control, brainwash, and feed off of. Let’s remember just what helps make us unique and what develops our talents, as well as the great examples of homosexuals who have gone before, stood apart and who have changed history for all mankind. Now, that is something worth cultivating, worth learning from and even aspiring to and it takes a lot more than learning to “date” someone is pants and looking for a Mr. Right to win an imagined lottery that will answer our prayers, make life complete and satisfy every need. Overt (mainly Victorian) romanticism just sugar coated the heterosexual imperative of property and paternity driven marriage. Gays have another whole universe to explore and many dimensions to relish if they just don’t get bogged down in the heterosexual ideologies. LOL

  • Jui Cy

    Mark Echenique

  • winemaker


  • Luke Ellison

    Dont agree with 10. I always go halfsies then if there is a 2nd date I pay. That way if the 1st was a bust didn’t cost u so much.

  • 1898

    @Luke Ellison: Good point. I think #10 should be negotiable. I mean I like the idea of “if you asked him out, you pay” but that’s not always practical. Recently a guy asked me out, and he had to drive 1.5 hours to get to me (his choice, he didn’t want to meet up in his own area because there’s nothing to do there), so I offered to pay for the meal because of the distance he drove.

    Otherwise, I do find splitting the bill to be less awkward and it helps prevent any feelings or perceptions that one person was more invested in the date than the other.

  • andrewl

    EvonCook well said indeed. I realise the article is a bit of froth but really the ‘dating’tips could have come from a magazine like Dolly or Cleo (I am Australian these were magazines targeted towards girls and young women). Really the only dating tips or hints are:-
    1) be polite and treat the person you are dating with respect
    2) treat your self with respect
    3) be true to yourself
    4) enjoy yourself
    5) be safe and don’t do anything your aren’t comfortable with

    All the other crap about how many times you should ring or who should pay is fluff.

  • sesfm

    And also, sadly: Be attractive, because gay men consider it rude to be ugly. I’ve seen gay men be offended that an ugly man dare speak to them on Grindr. The mere implication that the ugly non-human would have a chance with the man in question is taken as a grave insult. This rule of gay etiquette applies even more strongly when approaching in person.

  • Talisman

    Excellent Suggestions, DR. I couldn’t have written it better myself. It sound a lot like the book “It’s Just a Fuc*_ng Date.” Such good advice. We all innately know it; it’s just whether we apply and follow it. Thanks for sharing. Hope life is treating you well.

Comments are closed.