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NotGod_DavidBowie asks:

Advice for a 27 year guy who just got out of a long-term relationship? I’m talking really long-term for my age. I’ve been with this girl (apart from some short breakups) since I was 17. I don’t need advice on how to handle the breakup. I’ve been through the situation before and I’m very experienced on how to deal with it, and mature enough to realize that it’s permanent this time. What I am worried about is that I haven’t seriously dated in 10 years and have no idea what I’m doing.

  • What’s the best way to meet/talk to women?
  • What can I do to make myself more attractive (besides working out/losing some weight, dressing better)?

I have a nice place to live, decent job, 2 vehicles and I think I’m reasonably attractive, besides being a little bit out of shape.

Demetrius says:
 There are a few things that I found interesting about your question. Not only the length of time that you were in a relationship, but also the fact that you think that you’ve been through this situation before and that you’re experienced enough to deal with it. I appreciate your confidence, but it is misplaced UNLESS you plan on getting back with your ex. You’ve never broken up before, you’ve been on breaks. A break up is an ending, and if you went through a few “short breakups” they weren’t really break ups at all and you shouldn’t think of them that way. If they were short, you very likely didn’t try to date anyone else in earnest, or really dive headlong into the dating world and how different it is ten years later. Otherwise, you’d have some idea of how to seriously date. That’s just my opinion and it might come down to a semantic issue, but I’d urge you, and anyone, to not assume that they can handle anything about a breakup.

That said, welcome to the future, baby! Did you know that you can now send and receive HD quality photos of genitals on your phone? What A Time To Be Alive. Seriously though, dating as a whole has gone through some pretty significant changes in the last ten years when it comes to how we facilitate dating, but the actual dating hasn’t changed all that much. Sure, there will be people who write hot takes about how the advent of mobile-only dating apps has changed how we get dates, but how people actually date hasn’t changed all that much. Some people want hook ups so they seek them out, some people want relationships and seek them out, and some people want ethical non-monogamy and seek them out. We still date the way we did since 2006, it’s just how we get those dates that’s changed. If you want to meet people who are only looking for a seriously relationship, it really wont matter to you whether or not MOST people use certain dating apps primarily for hookups or not. You know how at one point singles bars didn’t exist? Then they did exist and it was revolutionary but there were still plenty of people who didn’t meet their spouse at a singles bar? Yeah, that’s how you should think of Tinder and it’s ilk. Yes, people do use the Tumblecupid’s of the app world to meet and hookup, but there are plenty of people who don’t date online, or those who do date online but aren’t hook up focused.

What’s the best way to meet women? Depends on where you live, if we’re being honest. If you’re a New Yorker like me, and a straight man, a healthy mix of online and offline dating will work for you, but you could also just choose one or the other and you’d have no problem dating. There are slightly more single straight women in NYC (53%) then there are single straight men (47%) in New York City, so it’s a buyer market for men. Part of me, the smart part, is guessing that you don’t live in NYC because you have a “decent” job and 2 vehicles. Can’t do that and live in NYC if you’re single, so let’s just say you live in a small American city, and we’ll use Cleveland as a proxy for whatever that city might be. With a small city in the US, like Cleveland, you’d be safe doing both online or offline dating, because the population of Cleveland and its surrounding area is about 2.6 million. In your specific case, I get the feeling that you maybe can’t leverage your friends who might be single in your larger friend group because after 10 years you probably share most of your social network with your ex. If that’s the case, you can always join social sports leagues to meet people, Meetup groups, and so on. I’m a big fan of social sports leagues because it involves socializing, drinking (if that’s your thing), and being active which serves the added bonus of helping you to be active and potentially lose some weight. If you live anywhere with a population of 1 million or less, you really should be dating online, purely because it’s smart based on the numbers. You don’t want to limit your options. In most places in the US, only about 13% or so of the population is between 20–29, so just keep in mind that if where you’re dating only has 10,000 people, your potential dating pool is something like 6500 people (13%, divided in half assuming 50% are straight women).

When it comes to actually talking to women, here’s something to remember: You’ve had practice talking to a woman you’re attracted to. I think that 10 years worth of a relationship will translate into you being fairly comfortable with making small talk with women. Don’t turn women into some inscrutable monolith who you have to talk to in a special way, just try to remember that you’re probably more experienced with talking to women then most single guys at 27 years old. I would hope that you know how to have mature discussions with women considering you basically grew into an adult right alongside a woman. Talk to women the way you would with your ex, minus the pet names and inside jokes of course. Flirt, engage and listen, respond to what you hear, and ask open-ended questions. Don’t bring up the significance of your last relationship or it’s length too early on, just acknowledge that you’re single now and looking to date. My favorite tip to get people more acclimated to talking to strangers is to try flirting with someone you find attractive with no goal in mind. Try flirting with people you’d want to date, build up your confidence, and just see where things go. If you have a goal in mind, like getting a phone number, you’ll become rigid, mechanical, or just too goal driven to get comfortable enough to talk to new women. Don’t approach talking to women like a salesman, treat it the way you would getting to know a friend of a friend. Keep it low pressure and loose and you’ll build an easy confidence.

What can make you more attractive, besides the obvious of course, is learning to embrace and appreciate how you look now. Working out, losing weight, and dressing better are great ways to appear more physically attractive (not that not being fit is inherently unattractive) but those are things that take time, and money. The easiest fix I’ve found is acceptance and appreciation of who you are, right now. Your acceptance of your flaws is a great confidence builder, and confidence is sexy. I am not, nor have I ever been very fit and unless some magic fitness pill is invited tomorrow. I’m probably in the same boat as you, if we’re being honest. We can be honest with each other right? You know what, I think I look fucking great, even if I am out of shape. I might not have the abs of Ryan Reynolds, but I think I’m sexy, and there are like, a couple of women who also would agree with me. That confidence makes me a bit sexier than some bizarro version of me with a six-pack who isn’t confident about his body. Speaking from my own experience, I’d rather date the woman who is a bit soft in the mid-section but comfortable in her own skin versus the super-fit girl who I can’t eat or drink with because she’s afraid of how that will change how I view her. Oh and smiling works a lot. Seriously, just generally looking approachable is a good idea. It’s okay if you’re not naturally inclined to smile, but just be aware that a smile is inviting and a frown or a pout is not. Oh and this might sound a bit silly, but the best way that I’ve found to figure out how to be more attractive is to ask a very honest woman her opinion of your hair, your facial hair, your grooming and hygiene, and most importantly your footwear. Basically, anything that can be quickly fixed. This is not a joke in the slightest. You don’t have to take every single suggestion, but sometimes people value comfort over attraction when they’re in a relationship, which is fine, but when you’re newly single it’s a good idea to reevaluate your look. Your girlfriend could have had weird preferences when it came to how you style your hair that literally no other woman would think looks good on you. Speaking from personal experience, every time a woman has made a suggestion to me to change something about my look, whether it was getting rid of my facial hair, or wearing more form-fitting clothing despite my less than perfect physique, it’s worked out way better than I expected. Dress, groom, and style yourself for you first, but women second. Don’t do anything that will make you wholly uncomfortable or out of character, but be open to making tweaks here and there. I am eternally grateful to the girl who suggested that I get rid of my mustache because it made me look pervy. Who knows what that equivalent is for you?

Most important though, just have fun man. Enjoy being single for what it is, and have fun.

Good Luck Out There.

Filed under: Dating & Relationships Tagged: advice, Casual dating, casual relationship, casual relationship advice, dating, Dating & Relationships, dating a friend, dating advice, dating advice for men, dating advice for women, dating and relationships, dating Q and A, Dating questions, dating questions and answers, online dating, relationship, relationship advice, relationships, self help

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