Random & Tweetable Dating Tips For Guys Of A Certain Age

Some of these might seem patently obvious but each one is based on women’s actual dating and attraction experiences. Feel free to tweet these to your followers or add your own random dating tip.

  • If it’s a first date from online dating, go to a place without bright lighting.
  • If entertaining a lady at your place, keep chilled water in your bedroom. Wink, wink.
  • Shoes and wristwatch, keep them classy and elegant. Women immediately notice this and judge you for it.
  • Stand up straight, sit up straight, walk straight.
  • Women want you to boldly approach them. It’s a sign of confidence. Only do so in a safe environment.
  • When starting a conversation with a woman, never compliment below the neck.
  • Get out of the house. Run single errands on different days of the week.
  • When walking with a woman, offer your arm. Don’t hold her hand.
  • Even if it’s her car, you drive it when on the date.
  • Worst first date: Dinner and a movie.
  • When standing, keep your hands out of your pockets. Pocket thumb hook, cowboy style, is acceptable.
  • When walking, look at the horizon, not the ground.
  • Speak clearly. Too much “Um” and “er” kills conversation.
  • Dress one level up from all the guys around you.
  • If you don’t want to text, you don’t want to date.
  • Put your name at the end of your outgoing online dating messages.
  • If you get the date, don’t over-communicate with her before the date.
  • You want to give a gift on the first date?! Don’t be a moron. You barely even know this woman.
  • The future of meeting women will be singles events in real life. You do remember real life, right?
  • Do you feel compelled to talk about an ex on a first date? Stop dating. Recover emotionally first.
  • If you don’t have the time to date, you’re not ready for dating.
  • Fingernails, clean ‘em and trim ‘em.
  • That haircut of yours sucks. Trust me on this.
  • The point of online dating is to actually go on dates with real women.
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  1. #1 by Natty Shafer on May 10, 2013 - 6:11 PM

    Skittles are perfectly fine to give as a gift, first date or not.

    • #2 by LostSailor on May 10, 2013 - 6:36 PM

      Damn. Beat me to the Skittles reference. But still not a first date option. Maybe second date, if your game is tight…

  2. #3 by LaRubia on May 10, 2013 - 6:22 PM

    Curious about why you say that dinner and a movie is a “worst first date.”

    • #4 by Natty Shafer on May 10, 2013 - 6:29 PM

      First, because you spend half the time in a dark theater, not getting to know each other, and second because it’s rather expensive considering you don’t know if you like the person enough for a second date. That’s a lot of time commitment and money commitment for no guarantee of anything, ever.

    • #5 by LostSailor on May 10, 2013 - 6:40 PM

      What Natty said.

      First date is never dinner (though if it’s working, maybe light apps), let alone a movie. It’s determining if she’s someone you’d want to see again and building attraction. Dinner and a movie is for when you’re already very comfortable with each other and shagging shamelessly. Dinner and a movie is when you want a break from shagging. (well, at least maybe as a prelude. If it’s a good movie.)

  3. #6 by LostSailor on May 10, 2013 - 6:35 PM

    Chilled water in the bedroom? Solid gold.

    I don’t wear a wristwatch or any other jewelry. But my boots are always shined. Except the snakeskin ones. But they still get noticed. And serve to weed out the PETA loonies.

    Always offer the arm, it’s classy. Never hold hands in public.

    Hands out of the pockets is key. I have forced myself to use the hands-on-hips, what used to be called “arms akimbo.” Classic power stance. Pocket hook is indeed acceptable.

    Yes, put your name on outgoing dating messages, it’s reassuring and makes you a real human, rather than just an online fantasy. And look to see that women do the same. If they don’t early on, be wary.

    The “gift” on a first date is that you agreed to meet them. Generally, don’t give gifts at any time. Unless she does something extraordinary, and even then, a bag of Skittles is acceptable.

    Definitely trim fingernails (and toenails). You assume you’re going to get frisky-time, so be prepared. Too-long nails during certain, uh, intimate activities will get you kicked out damn quick.

    My haircut is great. Find a good barber and pay to maintain. You probably don’t need “product.”

    And if you’re online dating, but not actually going on dates with real women in real life, you’re not dating. Stick to porn until you’re ready.

    • #7 by AverageMarriedDad on May 10, 2013 - 10:35 PM

      Agree on all points but the product one. Depending on hair type, product can make you or break you regardless of cut. I’ve used a lot, but bedhead wax is working as a pretty good all around item for me right now.

    • #8 by Johnny Caustic on May 11, 2013 - 4:08 AM

      I gotta disagree on “product” too. I’ve reached the age where I’ve got a thick corona of flyaway hairs, which makes me look like a stray dog. A little product makes a world of improvement: I put a thin layer on my fingers and very lightly float them across my wayward hairs until they hunker down with the rest of my hair. Suddenly I’m Mr. Elegant.

      Learned it from my overpriced hairstylist. I’ve started noticing a lot of scraggly women who really need to learn the same trick.

    • #9 by Phoenix on May 11, 2013 - 4:31 AM

      Don’t do porn lol. You need the testosterone to feel good.

    • #10 by LostSailor on May 11, 2013 - 8:49 AM

      Well, I probably have an aversion to “product” because my Dad used to slick his hair down with Vitalis by the gallon.

      And if a man is doing online dating but not actually going out to meet women in the real world, low T from porn is probably the least of his worries…

  4. #11 by Chewie on May 10, 2013 - 8:56 PM

    Solid stuff. It’s not my demographic, but it’s good. I’m curious about driving her car while on the date though: Anyone have any stories or field reports about this? I’d never considered this idea before.

    • #12 by Chewie on May 10, 2013 - 8:57 PM

      Fixed the website link.

    • #13 by Johnny Caustic on May 11, 2013 - 4:12 AM

      A friend of mine dated an Indonesian girl who insisted that he always drive when they were in her car. I think it’s safe to infer that most American girls feel the same way but are less likely to admit it.

      • #14 by Phoenix on May 11, 2013 - 4:35 AM

        The man HAS TO drive. That way he can keep his mouth shut and enjoy directions while the girl blabbers on about random bullshit.
        Only time I let a girl drive me is after I’ve banged her.

  5. #15 by dannyfrom504 on May 11, 2013 - 4:46 AM

    i happen to think my haircut is just fine.

    • #16 by theprivateman on May 11, 2013 - 9:12 AM

      I actually had you in mind when I wrote that about the haircut. Wokka wokka wokka.

  6. #17 by curious on May 11, 2013 - 11:05 AM

    What’s the chilled water in the bedroom for?

    • #18 by theprivateman on May 12, 2013 - 2:21 PM

      For the after-sex beverage.

    • #19 by smoothreentry on May 13, 2013 - 9:45 AM

      I’m glad someone else asked…I didn’t get it either.

      I like to ask her to get one out of the fridge because I like to watch her walk away…

  7. #20 by J on May 11, 2013 - 1:31 PM

    Good tips. The importance of avoiding too much pre-date communication can’t be overemphasized. Also, looking forward to your new line of PM-approved shoes, wristwatches and grooming products.

  8. #21 by BuenaVista on May 12, 2013 - 11:05 AM

    Great checklist. I fly and we use checklists for everything, even the simplest tasks, and especially in emotionally-frought situations. Dating can be stressful. I have a pre-date checklist (to which you just added a couple of things, thanks) to get me focused on how I want to behave and appear.

    I walk on the right (curbside) and wait for her to take my arm. If she does it’s a major IOI. And women almost always comment on the gesture of walking on the right.

    I also will ask her what she would like to eat or drink and just order for her.

    I dated a Hollywood (producer’s ex-) woman for awhile and have retained their fashion bias. Black tailored suits, flat front pants, open collar most of the time. A simple uniform, easy to find and maintain, and almost always positioning you above the herd. Also versatile enough to take you from a fancy event to a dive bar for close conversation. Get it tailored no matter what, and remember most men wear suits that are too large. Two inches between button front and abdomen, no wrinkling or crimping in the shoulders, quarter inch of shirt cuff visible. You can buy an inexpensive suit from JosBank and get it tailored for less than $350, and beat the hell out of it for a couple of years. Cost per use maybe $10.

    Women obsess on their jeans and how they fit their butts. Pay up and get something not available in a shopping mall and and make sure you don’t have diaper butt. With jeans I always wear a jacket. In summer the jacket is seersucker or linen. Don Draper wears a jacket to go pick up the kids for the weekend.

    Spills happen. Carry a handkerchief and clean it up for her. They’ll remark on that, too. Don Draper has a handkerchief at all times.

    Also, I spend more on shoes than I do, often, for the rest of my clothing. Women with any style aren’t going to get fluttery over a guy with crappy shoes. The target/aura shoe for a lot of women is Manolo. Manolos cost $500+. Men are lucky because a $500 pair of shoes will last for 20 years, and your cost-per-use will be below that of a $100 pair of shoes, which are done in a year or two. I have only two accessories: a watch and great shoes.

    In general I have found it useful, in any dating environment to ask WWDDD (what would Don Draper Do). Even Marcotte is obsessed with Don Draper. I date the 35+ cohort though; no clue if a 20 something has ever even seen someone with manners.

    • #22 by smoothreentry on May 13, 2013 - 9:47 AM

      I have never watched an episode of Mad Men. Is it worth watching the show just to pick up on the Don Draper character?

      • #23 by BuenaVista on May 13, 2013 - 1:20 PM

        I think he’s a complex, interesting character in a series that is perhaps the most focused on, and successful at presenting, style (both in terms of Draper and Roger Sterling). Draper is a quiet yet dominant presence in every room, and someone who clearly has boundaries and standards that he will not allow to be crossed. If you like the show, go back to the first seasons; I think that they offer more interesting narratives. I watch almost zero TV not involving a baseball, but I have seen every Mad Men episode.

  9. #24 by Dr. Faust on May 14, 2013 - 11:01 AM

    Hands in pockets is not a bad sign. In fact, it could be a plus since it presents a mystery.

  10. #25 by DDDD on May 16, 2013 - 6:52 AM

    Turn on some charm like Don would do, but please, guys, nothing else…
    Don’t Do Don Draper (DDDD)

    His character is a sociopathic narcissistic cheating alcoholic, and any self- respecting woman in the real world would run at the first sign if a scoundrel like that.
    If you want notches, play the Don Draper game, but you will NOT be getting the quality of characters he gets on the show…
    You’ll be getting the damaged goods that are too stupid to notice the game or that have ridden the carousel so much that they know that this is all they deserve…
    That is all :-)

    • #26 by LostSailor on May 16, 2013 - 7:56 AM

      His character is a sociopathic narcissistic

      Which, of course, is exactly why he is so attractive to women. Women in the real world would flock to him, regardless of self-respect. Yes, even “high-quality” women. Why? Because he’s also outwardly dominant, charming, and highly successful. The thing with truly sociopaths and narcissists is that you don’t find out until long after the fact.

      Actually, “playing” Don Draper game will still attract those same women, and when you slowly reveal bits of the good man underneath, you will be able to keep them. If that’s what you’re looking for…

      Aside: are you really a size DDDD? Pics or GTFO.

  11. #27 by Ton on May 17, 2013 - 2:54 PM

    The fashion advice is interesting. I’m a meathead, no neck, crew cut, mutton chops. I dress in workboots, jeans, Hawaiian shirts/ t-shirts, and wear a Stetson. I tried suits and the like last October and my success rate went down. Initially I chalked it up to the style of dress being very common in Raleigh, but now I am wondering if it’s a matter of body type.

    Any input from the brother’s who know these things?

    • #28 by LostSailor on May 17, 2013 - 3:17 PM

      I’d ditch the workboots and the Hawaiian shirts, unless you’re at a Jimmy Buffet concert. I’ve been wearing Western boots in NYC for years (very comfortable, BTW) even though I’m from New England, and it’s a style that sets me apart. It probably is a matter of body type. If you’re going to wear a suit, and it’s not a bad idea at all, you need to spend a little coin, it’s well worth it. You want high-end fabrics, and I would strongly recommend springing for a tailor-made suit. If you do have to go off the rack at, say, Men’s Warehouse or a department store, don’t have them do any alterations because they suck at it. Definitely find a competent tailor–one whose sole business is being a tailor, not the guy at the dry-cleaning place. Have him do any and all alterations to make the suit fit your body-type the best (talk to him before you buy as he can probably give you better sizing information). If there’s a place in town that does custom-made dress shirts, they are well worth the investment. Oh, an no pleats in the trousers. Just, no…

      • #29 by Ton on May 17, 2013 - 8:00 PM

        Thanks bro. I think I did it right. Wardrobe was the 1st thing I wanted to fix when my income went up and I did a fair amount of reading, checked into a few shops and went with the one I liked the best.

        I spent about 6k on two suits, shoes, 3 days worth of casual wear etc. Most of that on the suits and a tux. Got them altered and all. My daughter and tailor picked out the style, colors, cuts etc. The payout in dating success has been pretty much 0. I’ve worn the tux twice, suit a few times times more, but meet the girls in the gym and the like. Stopped wearing the casual stuff.

        My wanderings are is it my build? spend enough? wrong style? To common place style or not applicable to the way I live and approach women? Does not have as big of an impact on younger women…

        Workbooks are a must, ride a bike most days. Do have some nice cowboy boots I wear when I drive. And the Hawaiian shirts are semi high end , most in the $100 range

        It’s always odd to me when my experiences don’t match the norm. Probably over thinking the whole damn thing

        Thanks again

      • #30 by LostSailor on May 19, 2013 - 12:05 PM

        It sounds like you did do it right. I have little use for a tux, though I do have friends who have bought them. And while I have several nice suits, I usually don’t have to wear them for work, but have worn them on certain dates. For me, I find either jeans or casual slacks and a good blazer are more my style.

        Suits work, but a lot depends on the situation or occasion. They’re not going to help much at the gym. In terms of dress, I think you have to shape both your personal style and your clothes to the surroundings, not to mention your target audience. It’s probably not your body-type.

        I understand the work-boots if you’re on a bike. But there are several manufacturers that make heavy-duty western boots (steel toe and shank in the insole) that might suit (so to speak).

        I, too, used to wear Hawaiian shirts, fairly high-end, but since that was back in my Blue Pill days, I usually don’t anymore, unless at the beach or relaxing over drinks after a nice summer afternoon sail…

    • #31 by LostSailor on May 17, 2013 - 3:18 PM

      Jeans and a quality blazer also work well. Same tailoring rules apply.

  12. #32 by BuenaVista on May 20, 2013 - 11:07 AM

    Draper is not a “sociopathic narcissist”, because he has empathy. He’s profoundly empathetic, actually, when he allows himself to be; he’s capable of love and sacrifice. True, he’s very troubled, and he’s often profoundly selfish, and he’s self-sabotaging (because of his enduring sense of shame, having been reared in a whorehouse). But sociopaths are easily identified by their total lack of empathy.

    The narrative of Mad Men is a compelling one because it is, at bottom, the story of a complex man in lifelong emotional free-fall (see opening credits). I predict that Don has only one way out. We’ll know next year.

  13. #33 by BuenaVista on May 20, 2013 - 11:23 AM

    Ton, the Dos Equis guy wears suits. If you don’t like suits or feel they don’t work for you, you might play this riddle-me-this game: if there is a female ‘type’ you like, try to figure out what her father wears when at a family reunion, church or a meeting at his lawyer’s. That might really float her boat.

    On the boot thing, I’m skeptical. I ride bikes too (Guzzi, yeah) but I don’t wear my road protection on dates. BUT. Because I like boots, and I want my women friends to think of me as a guy who rides bikes, tractors and can re-shingle a house, I often wear boots with jeans and a good jacket when out on the town — whether it’s Sioux Falls or New York City. I bought myself some Justin lacers, had the bootsmith replace the rubber soles with leather and add a half-inch to the heels, and I keep them polished up so no one confuses them with workwear or bikewear. Total cost: $180. I wear these boots to the Princeton Club, the Carlysle, and dive Irish mafia bars. So I am either in jeans and a jacket, or simple black suit (and repeating above: no fucking pleats, especially if you’re built more like a linebacker than a distance runner). I wear my boots nine months of the year with jeans, Brooks Bros. shoes with the suit, and very good loafers (polished; no one seems to do that anymore) in summer. Even my daughter, who works in fashion, says I’m a conservatively dressed clothes horse, but in truth, I just have two uniforms with two dominant colors (black and white), and it’s easy to manage. Also, Brooks Brothers button down shirts, starched, look good with absolutely everything, though it is a conservative look. They also last for 15 years, even if they are professionally laundered.

    For upscale (status indicator), more manly wear, check out Filson or maybe Orvis. Maybe a waxed cotton jacket from Belstaff (used to just make bike jackets for Brits). (I have a Belstaff jacket that I bought 30 years ago and it will outlive me unless I drop my bike.) Every guy should have a signature style, and if it works for you and the females, just stick with it. I never met a woman who got excited about dating a clothes fetishist. Clothes horse, yes. The fanciest woman I dated in the past 10 years was emerging from a Hollywood marriage; she never stopped complimenting me on my very simple dress code.

    • #34 by LostSailor on May 20, 2013 - 2:04 PM

      Gotta echo what BV says here. I, too, really have a limited number of “signature” styles that are very easy to maintain. But I wear boots with practically everything–though I do have a couple of pairs of high-end dress shoes that I wear on occasion. Boots are Western round toe (not the really pointy ones) in basic black (the everyday boot), “weathered” brown/tan that don’t need polishing (though do need occasional conditioning), and burgundy python-skin, which I wear with anything as the mood strikes. The thing is, the boots are the most comfortable footwear I’ve ever had. When the soles go, which they do with city walking, there’s only one cobbler I take them to in Manhattan where they do only shoes and leather (not a dozen different sidelines like most shoe repair) and they only use quality leather soles. It’s a little expensive and they take only cash, but worth it. Usually get boot mail order, since I’ve had my size measured from Cavender’s. Next up: ostrich.

      Since I don’t normally have to wear a suit to work, I’m usually in boots, jeans, and a blazer in warm weather. I also have a 30-year-old hand-me-down brown motorcycle jacket that my brother gave me years ago. While I couldn’t wear it for years in my overweight/beta/blue-pill days, it fits fine now; a classic style without all the belts and such. Now, since i rarely weigh myself, it’s my weight guide: as long as it fits, I’m good. But it’s on it’s last legs having been repaired so much, so I may have to replace it soon.

  14. #35 by BuenaVista on May 20, 2013 - 4:01 PM

    Perhaps another thing Ton could do, if he’s interested, is ask himself (irrespective of female preferences), which movie star in which movie (in his dress) do I wish to emulate?

    In my case, I copy Gere. Whether he’s a cop, or a banker, I dress like Gere. That’s where I’m comfortable. He’s wearing jeans, or he’s wearing a black suit. So that’s where I live.

    I also simplify, iron, starch and fold, like Vin Diesel did in some idiotic romantic comedy he was in where he played a SEAL. (Summer? Pressed khakis and bleached white t-shirts. I got some organized dresser drawers.) I teach my Chinese lady launderer how to do my shirts right. (e.g., no starch in black shirts: they’ll shine.) Enlisted Marines have good clothing discipline: it’s clean, it’s pressed, it’s durable, it’s shined, it’s consistent, and it’s cheap. And no one thinks enlisted Marines are pussies. But they know how to iron, don’t they. And they look sharp. I’m better at ironing than most of my girlfriends.

    • #36 by LostSailor on May 20, 2013 - 4:35 PM

      Yes, amusing isn’t it? I can iron and frequently do my own shirts to save money (though prefer to have the laundry people do it, at least with the off-the-rack shirts; I try to do the custom-made ones since they’re pricer). I’m also a better cook than my ex or any girlfriends. I can also sew (if you’re repairing torn sails, you want to make sure those suckers are done right…).

  15. #37 by Drew on June 4, 2013 - 11:16 PM

    “Pocket thumb hook, cowboy style, is acceptable.”

    Just an FYI to be careful. Hiding thumbs is low status. Displaying thumbs in a genital frame is high status. Hooking thumbs in loops is closer to hiding than displaying and therefore probably low status.

    Source: What Every Body is Saying by Joe Navarro Retired FBI Agent

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