For the Thirty-Somethings: The Dating Jungle

By: Judd Livingston

Welcome to Part 2 of Judd Livingston’s look into dating and relationships for women in their 30s. To check out Part 1 and the comments click here.

Last week we spoke about the reasons why many men are no longer seeking out the trappings of marriage and how that’s affected women. That was all very well and good as interesting information, but it didn’t offer any specific suggestions on how to use that information. This week, that’s what we’ll do: look at a few different, simple things you can do to increase the chances of you connecting with a guy who wants to connect with you. While finding a mate may be hard, it’s certainly not impossible. It’s all in the way you play the odds. What I’m going to suggest isn’t magic or a guarantee, but it will certainly tilt things in your favour.


In the last article we mentioned the motivations, or lack thereof, for men to marry. The important thing to remember is the fact that many men still see marriage as an important part of their personal lives. Those are the men we want to target, so let’s look at ways in which we can trim the fat and focus on the prime beef that is the Marrying Kind. Usually, from my understanding, the problem doesn’t lie in getting dates, it’s what happens after that’s the problem. Either:

a) you don’t like him but you “want to give him a chance” – You don’t connect with him.

b) you like him and he doesn’t want anything “serious” – He doesn’t connect with you.

In the first instance, this is your mistake. I’m not saying you shouldn’t give someone a few dates to get to know them, but if you know you have no real interest in the guy, don’t waste your time. Or his for that matter. The only reason you’re doing it is because of your fears. Your fear of not finding another guy after this one, your fear of being alone, whatever. Who hasn’t said to themselves at some point “But what if this is my last chance?! What if HE is the guy?!” Let me tell you, those fears are unfounded. You snagged a date with this guy after the last, no? Then why wouldn’t you be able to get a date with someone else once you dump this one? Just bail on him if you’re not into it.

The second part is the real issue. Women frequently hang on too long with guys who they like despite the guy giving her allllll the signs that he’s not connecting with you. Part of the issue is that, even if a guy isn’t “connecting” with you, he may still very well want to have lots of sex with you all the time. This might lead on, logically, to believe he’s looking for something serious, when all he’s looking for is casual sex. Sometimes guys even come out a say, very blatantly, that they don’t want anything more than sex, and even then, women frequently delude themselves into believing it’s a good idea to stick around. I’ve heard a myriad of excuses: “Well, all I want is casual sex as well!” Oh really? Then how come last week you were saying how much you’re liking this guy and how excited you are and you think he likes you, etc. Don’t lower yourself to that point; the point where you’re changing what you want in the hopes that eventually he’ll change his mind. And don’t believe that you can change his mind, regardless of how awesome you are. So, first and foremost you need to start being honest with yourself and end things as soon as a) you realize you don’t like him; or b) you realize he doesn’t like you. But what if he doesn’t tell you he’s not connecting? Well, you could always ask, but that’s a totally unnecessary question because you can simply use your powers of observation; the signs are there.

You’ve been seeing this guy for a while, and are wondering whether he’s into you, or just looking to hook up. Just as Deep Throat told Bob Woodward to “Follow the money,” you should be following the sex.  Ask yourself this: has he ever asked to hang out with you before 8pm? I don’t mean dinner reservations at 7, I mean has he asked you out during the day when the likelihood of hooking up is significantly diminished? The odds of having sex at night are way greater, usually because alcohol becomes involved, something that doesn’t often happen at 11am. If you want to know if a guy really likes you, get him to spend a significant amount of time with you during the day. An activity where no alcohol is present and the odds of sex are minimal. Get together for brunch and a walk in the park, followed by a trip to a few galleries, then a late lunch. Why? Because a guy will get frustrated if he doesn’t really like you. If he’s just using you for sex, he’ll know that he’s not getting any and he’ll start to be mad: “Why the hell am I out here with this broad?” I know this because I’ve been that guy. I’ve been able to get through movies, plays, dinners and drinks, whatever, with people I don’t like all because I know I’ve got a good chance of getting laid afterwards. A few non-sex, day-dates will bring his feelings right out into the open. I’ve had a few female friends try this out and you’d be surprised how hard it is for them to get the boys to accept a Day-Date. “Ohhhhh, I’m busy but I could totally meet you later on.” Because all these guys want to do is bang.  Another option is to choose a date activity he’s not super into, or something rather long and inactive (i.e. watching a baseball game). Doing so forces the date to be about the actual interaction. It becomes about the two of you and not what you’re doing. If he’s into you, this is an awesome day with an awesome girl and the events themselves are simply incidental. If he doesn’t like you, and doesn’t like the activity, he’ll get restless. Again, I know this because I’ve been that guy and I’ve gone on amazing dates with amazing girls while attending a function I couldn’t care less about and vice versa.

Another sign to look out for: the disappearance. Frequently I hear girls say their guy hasn’t returned a text/call/email in almost a week and they’re worried he doesn’t like them anymore. Fact: he never did. I almost always tell them “Wait for a few more days and see if he doesn’t contact you. Because he will. Because he’s horny.” No man is so busy that he can’t contact you for many, many days. Even if they’re in Bangladesh for work. They could have sent you a text in the cab ride to the airport, while waiting at the check-in line, while having a couple pints at the airport bar pre-flight, from the hotel through the wifi. If he doesn’t text you, he’s not too busy, he’s just not horny anymore. After a week without sex, he’ll be raring to go. A buddy of mine once put this quite eloquently: “Chicks think all guys care about is sex, but that’s just not true! It’s just that, you only see us when we want sex. When we don’t, we’re busy playing video games, watching sports, eating sandwiches and drinking… with other guys.” Nothing more accurate has ever been said.

There are plenty of other signs, but the real lesson here is to be completely honest with yourself. Also, listen to your guy friends. If they say “Dude’s just into sex,” believe them. And don’t convince yourself that you are too. You’ll end up wasting time and effort and emotion for nothing. Jump ship and start looking for another guy.

But before you go and start that search, it might help if you were to take stock. This is a more passive exercise to help you land a  man, but it can be very helpful. You need to figure out exactly what you want in a man. I don’t mean tall, dark, and handsome, I mean values, morals and all that junk. The physical stuff will sort itself out instinctively, it’s not something you need to dwell on because our bodies give us plenty of signs that let us know we’re physically compatible. That being said, don’t convince yourself you have a “type” and limit yourself to it. I’ve seen many girls do this, saying things like “I want a guy who has blond hair, blue eyes, etc…” and then end up falling in love with a wonderful man with dark brown skin. It’s about as dumb as me saying “I only date blond chicks with big boobs.” No brown-eyed, dark haired girl wants to hear a guy say “I only date big breasted blue-eyed blondes,” because they’ll feel unfairly cut from the pack despite their many amazing qualities (including their beautiful brown-eyes). So if you don’t like it when guys do it, don’t do it yourself. There’s plenty of guys out there who might fit your physical criteria, but nothing else. Those are the guys who you feel connected to, but just want you for sex. If you allow your instincts to focus on the physical chemistry, and you focus on the rest, then you’re more likely to find a deep, meaningful connection.

To help with this exercise, take a look at the guys you’ve been dating in the past and see if there’s any positive pattern you can find. What kind of guys are you drawn to instinctively and what qualities are they holding. Then, look at patterns for negative characteristics. Generally, while we think we might select our partners from a broad spectrum, they generally have more in common than we think. And sometimes the qualities we look for can be paired naturally with characteristics we dislike. Again, this is a large generalization, but there’s some truth to it. For example, if you tend towards an investment banker/lawyer/rich guy who makes a ton of cash and drives a sweet car and has an expense account, you might be attracted to the notions of security, stability, power. But the cons that come with this might be that: he’s a Type-A who’s a workaholic and also a bit arrogant and he might eventually lose focus on you and return to his work. If you want a cop/fire-fighter/EMS type of guy who can save lives and will ravish you, maybe you like feeling safe and protected. But remember that: they work in shifts and have incredible stress levels and are part of marriages that happen to have the highest rates of divorce of any professions.  If you want a musician/bad boy/tattoo artist maybe you’re attracted to excitement and danger and the thrill of an unorthodox lifestyle. But remember that: that lifestyle tends towards drinking, partying and doing drugs, a notion of freedom from responsibility and commitment and not many nights in. If you’re looking for an athlete, a hockey/football/baseball player, be aware: the culture within sports is inherently misogynistic and within it women are seen as points to rack up.

Are these all sweeping generalizations? Yes. Absolutely. Is a hundred-to-one shot horse guaranteed to lose the race? No. Not at all, but the odds are against him. I know men in all these professions. And they are not all as I have characterized them but many of them are. So, if you have a fantasy for any of these types of guys, try and understand what those fantasies might mean and then remember that, while these qualities might present themselves frequently in a certain population, they are by no means exclusive to that population. You can have someone who possesses edgy, bad boy characteristics, but has a stable job and lives clean. You can find someone who can provide you with feelings of safety and protection who doesn’t work in a profession with incredibly high stress levels and long hours. You can find an incredibly fit, athletic guy, who’s never been exposed to the culture of misogyny that is rampant in professional sports. Read Your Brain on Sex for greater detail and exercises on how to figure out what you’re really looking for in a partner and tricks on how to find it.  You can also sit down with a friend and chat about it. Meditate, pontificate, and actually give it some time. Knowing what you truly want makes looking for it easier.  Now let’s look at some active ways you can increase your odds of success.


First, online dating. You’re probably already on a few sites. It’s a no-brainer. But, make sure you pick a site that emphasizes relationships. The argument that you should join as many as possible to expand your dating pool is flawed: you’ll only be increasing the amount of jerks that you date. We want to cull the herd and leave only the most fit men. By joining a “relationship” site, you’re swaying the odds in your favour because the majority of guys posting will be looking for something relatively serious. Despite the commercials touting “scientific methods of matching” and bull like that, dating sites are quite simple: focus on a specific demographic. OkCupid, PlentyofFish, and the like tend to be populated by guys looking to get laid. Sure there’s a few others, but remember, we’re playing the odds here. When you get to the eHarmonies and Match.coms of the world, their demographic tends to be an older one, and a little more mature. The pay sites are especially successful at matching couples because those going into it are so serious about finding a relationship, they’re willing to pony up some dough. Doesn’t mean it’s a guarantee, but your odds increase. So eliminate any profiles you may have on lesser sites or sites known as “meat-markets” and if you’re not sure which those are, find a 25 year old and ask him. Also, look online for tips on how to tweek your profile, or read Amy Webb’s book, Data: A Love Story (here is Webb on the topic). I haven’t read the book, but the premise is logical: produce a profile that increases your odds of being contacted (and it’s not all about that profile pic).

But don’t rely solely on the internet. Our goal here is to be as effective as possible, which means we need to source our men from a wide variety of places. Let all your lady and guy friends know you’re looking. Your friends are generally not going to hook you up with someone they know to be playing the field if you’ve made them aware of your desire for a relationship. The same can’t be said for plenty-of-fish or the bar scene. Speaking of the bar scene: avoid it. Don’t bother. Here’s the thing: girls go to bars/clubs to have fun, dance with their girlfriends and to meet their next boyfriend/future husband. Guys go to clubs/bars for drinks with their buddies, to watch sports/listen to music and to fuck drunk chicks. Pardon my language, but I want to be very clear on this because it’s a huge mistake women make. Very few men leave the house saying “I hope I meet my next girlfriend/future wife tonight,” they say, “I pray to God I get laid.”  A lot of women reading this are saying “But I met my husband in a bar.” Great. I’m not saying it’s impossible, I’m saying it’s less likely. So let’s avoid it because our goal is to be meeting guys who are seriously looking for a serious relationship. Seriously. For the time being, the bar is just about you having fun with your friends, which isn’t a bad thing!

Be more active. Join intramural/recreational sports leagues. Take cooking/photography classes. Follow your own likes and hobbies and try to make them more social or public. If you don’t have any hobbies, now’s the time to find something you’d like to do. Sounds obvious, right? Well, the key is to flirt while you’re doing it. But don’t flirt like you would on a Saturday night after four cocktails. Flirt in the simplest of manners: by engaging. Have a conversation and be happy while doing it, with no presumptions or expectations. Flirt with a guy they way you would talk with a new female friend.

If you’ve been getting your flirt on in public and at your various hobbies, but the guys haven’t asked for your phone number yet, there’s a reason: it’s because guys are pussies. Which is the same reason why he’ll text first rather than call. It sucks that guys aren’t man enough to call you and ask you out on a date, but that’s the way the tide is turning now. They won’t ask because they will second guess whether they are reading your signs right. This truth can be multiplied when you’re flirting in the circumstances I’ve suggested (i.e. no alcohol). They aren’t at a bar, they’re in a cooking class with you, so they won’t be drunk enough to muster up the courage. Whatever the reason, guys are scared of rejection and guys are too stupid to understand when you’re giving us a green light. So, if it’s been a while and you know you talk to Johnny every Tuesday night at your French cooking class, and you’re always laughing and having fun, give him a bit of a lead. Help him help you.  Don’t ask for his number, just start a conversation near the end of class and when it starts to get going say, “I’ve got to go, but let’s get together to finish this later!” At which point he can say, “Sure, gimme your number”, because he’s certain you want him to take it. If he needs a little more prodding, you can simply add, “how’s next week looking for you?” to the above sentence. If you’ve got a hyper confident guy who’s got no problem asking for your number, great. If you’ve got a nervous kinda guy, push a tiny bit, but don’t be super-aggressive. There’s a lot of advice out there encouraging women to be the aggressor in dating situations, and yes it can work, but it can also be misinterpreted as desperation. The lesson here is to give us guys time. A friend of mine told me a story about how he kept running into this woman in his neighborhood, and the mutual interest was obvious, but he could never ask for her number. And he was always kicking himself afterwards. Finally, after the fourth random run-in, he did it, and was happy he did.

Hold out on sex. We kinda talked about this earlier when talking about going out earlier in the day. The premise is the same as the Day-Date: get him to spend more time with you without getting what he wants. Eventually, if all he cares about is sex, he’ll disappear. I’m not saying don’t have fun: Make out, fool around, but keep your shit together for the first three, four times. Then, move progressively into more intimate encounters. Ideally, we could take a page from the old school and you could hold out for months before having sex, but nowadays even a good guy would bail on you or assume you’re not into it. And don’t get naked on your first or second dates. Just kissing. Fully clothed. Outside your/his place.

Look at his other relationships. I don’t mean get his ex-girlfriends to write references for him, I mean find out about his non-romantic relationships. Find out if he has any female friends. Actually, find out if he has friends period. If he only hangs out with guys and women only pop up when he’s dating, that’s a bit weird, but not the end of the world. If he has no friends in town at all, unless he’s a recent transplant, it’s a sign that he’s not really the best at relationships. Look for a guy with friends, not acquaintances. If you keep hearing 2 or 3 names popping up, that means he has solid relationships with those people; try and find out how long they’ve been friends. If a dude has buddies from grade school/high school, beauty. If he has many circles of different friends, even better. Friends mean reliability, honesty, ability to commit, etc. Look for it.

In Blackjack you start off with the odds against you 51%-49%. By playing the cards right, and following certain basic rules as the game progresses, you can increase your odds so the numbers flip and it’s 51-49 for you. That’s what you want to do in finding a good guy: tip the odds in your favour. The above suggestions just scrape the tip of the iceberg when it comes to ways to do that. There’s so much more we could talk about, but really each case is very specific and unique. If you’ve got questions about a relationship you’re in, drop us a line in the comment section and we’ll do a follow up article with answers. Next week we’re going to look at something a little different: what if you really are the problem, not them? How to navigate self-sabotaging.

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