I’m tagging in the great Rob Overman to close out 2010. For those of you who are returning to dating or have never really done it, he offers a structured plan on succeeding at it, and I think it should be required reading in schools all over America. Instead, you’ll just have to read it here. I’ll have the second and final part up tomorrow. Enjoy.
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The New Year is upon us. And with it comes a slew of resolutions, many aimed at self-improvement and personal development (anyone else getting a shit ton of e-mails about the latest workout DVD?). If your New Year’s resolution is about lighting a fire under the ass of your dating life, this story of redemption is for you.
I was talking with a guy yesterday, and during the conversation he said:
“My entire goal for the New Year is to get a girlfriend. Like, a serious relationship – someone I can spend time with, ya know? Especially since it was just the holidays and my whole family kept asking ‘So is there anyone special in your life? When are you going to get a girlfriend?’”
Poor guy. Here’s a little of his back story just to give some perspective. He and his ex-GF broke up about two years ago. As far as I know he hasn’t dated anyone serious since then. In fact, I’m not sure if he’s even gone out on a date since then. And since he hasn’t really dated anyone, well, his game is probably a little rusty.
So here’s a question to the readers: How would you bounce back from this? If you’re basically starting your dating life over again after a breakup (or even if you never had a dating life in the first place) how do you do it? Seriously, I want to hear your opinions, leave ‘em in the comments below.
Here’s my take.
I’ve always said that when it comes to meeting women, you are either working or you’re playing. And if you’re not playing, then you’re working for it, and that’s not attractive.
But when you’re building a dating life from scratch, it’s going to take work. About a year’s worth of it, actually. So let’s get to it.
Get a Girlfriend Game Plan: January – April
I hope you’re ready to do some work because this is going to be your training time. Remember in “Rocky IV” when Rocky gives up his U.S. title to go to Russia and train all winter in the old barn? He lifts weights around his neck and does upside down sit-ups and jogs through the snow until he can outrun his Soviet escorts.
That’s you. You’re Rocky coming out of retirement. If you went up against Drago right now you’d get knocked out in the first round, so that means it’s time to train. Back in the day when I was younger and had just moved to the city I spent the winter slushing through the streets of NYC. I was inexperienced and outmatched.
I dressed with no style (though I didn’t realize it at the time), I couldn’t keep a conversation going, let alone make it fun or sexy, and I had no idea what to do if I actually did get a phone number.
So I trained.
1. Find a trainer. Luckily for me, I met a guy who would later become one of my best friends. He took me under his wing and showed me around the city. He was the type of guy who didn’t mince words: I remember one day I met up with him at a bar wearing a T-shirt over a button-up shirt and he said, “You look like an American Eagle store threw up on you.” It was a lesson learned.
One very important thing to look for in a trainer is someone who can help you from a position of love and respect. You want someone who will give you constructive criticism with your best interests in mind. Don’t just pick someone who, although they are good with women themselves, can’t teach it to you or just bust your balls when you go out. As the old saying goes, “Show me your friends and I will tell you who you are.”
2. Work on the Basics.You must, must, must spend the time slogging through the motions of starting a conversation. It doesn’t have to be pretty or smooth, but just get used to it. Sure, it’s scary sometimes and the pressure is all on you, but it’s important that you get used to that rush of adrenaline and work through your nerves to get the job done. Here’s a tip: don’t worry about what you say to start a conversation or even what she says back to you. Instead, think of what you’re going to say next. At this point you’re a stranger to her, so start by talking about yourself to de-strangerfy yourself. If she’s into you, she’ll start sharing stories about herself as well and after that it’s all downhill.
OK, that’s not true. There is still a lot left to work on when it comes to the basics. See the Big Four, for example. And I really recommend working with a coach to get the basics mastered, so if you have the time and are committed to it, give GK a call and tell him that you’ve got a little experience under your belt but want to know how to really maximize your time when you’re out.
3. Try, and Fail to get a Date. What? Fail to get a date? That’s crazy talk, Rob! You might think so, but I believe that we learn more from our failures than from our successes. During my own “training” phase, and especially toward the end of it, I began to notice that I was getting phone numbers every night
I went out, but very few of them ever turned into a date. What was I doing wrong? It took a few more months of trial and error to figure it out, but it eventually came down to how I “closed.” I’m not going to get into details here (again, call GK and set up a time to talk so that he can give you the best advice for your particular situation), but it turns out that I was acting too aloof when I got a girl’s number. Basically I was coming off like a player and they weren’t taking me seriously. I know, it surprised me too. Also, my phone game stunk, but eventually I smoothed it out into a formula that was pretty much foolproof. The funny thing is that I never would have gotten successful if I didn’t spend the winter walking all over NYC figuring out what I was doing wrong.
At this point you’re like Rocky running faster and stronger than his Soviet escorts. You’ve spent the winter training and getting better, but your goal might still be out of reach. In Part II, I’ll explain what I would do (and did) next.

{ 12 comments }
dating or lack thereof sucks in your mid thirties! Women my age are sitting at home with their babies and their fat hubbys. The women my age who are single are 50lbs over weight or have been through the ringer. my one piece of advice to all you younger guys out there – live everyday like it’s your last. You see a hottie you want to talk to, do it! If there are obstacles, walls and barriers to your girl, knock em down! date as many women as you can before 30. just remember, you can’t seduce a girl who is around her friends. seduction happens in private, like two teens all alone at mom and dads house.
The last part of my comment section seemed silly but I can’t believe how many guys I see actually think they are going to seduce a women in front of her friends, sisters, bosses, her mom!
Thanks for commenting, Johnny, and I know dating can suck at times. I’ve taken a little break from it recently myself. But I’ve gotta say, it sounds like your frustration is jading you. I don’t have the space here to give you examples of guys I know in their mid-30s who are having the time of their lives with one woman or several women — attractive ones, too. I’m included among those guys, as are some of my former students.
I seduced a girl in front of her friend just on New Year’s Eve — and I’ve done it more times than I can remember. Of course, there’s a time to be discreet, but sometimes if you can win a woman over in front of her friends or family, and those people like you, you will only help your odds later.
Rather than blame your circumstances, I suggest you do something about them. If you don’t like the women you’re meeting, meet them somewhere else. Women are waiting longer to get married these days (e.g. cougars) and taking better care of their bodies — come to SF sometime and I’ll show you. True, women can get crazy in their 30s, but we’re talking about dating here, not marriage.
You have touched on an interesting point, Johnny. Women in their mid thirties can be split into four categories:
1) Married, engaged or wifed-up. Kids in the picture or coming soon.
2) Too many head problems to date. Stay far away from these women. Their drama will cut you like a knife.
These are the two you mentioned in your comment and yes, they definitely exist. However, in the city I always found plenty of single, attractive women that wanted to go out. Most fell into the next category.
3) The Sex and the City lifestyle. These are the women who spent their 20s too busy to date so they live life to the fullest in their 30s. These girls love to have fun, but will run away from anything serious because it cramps their vibe. You can date these girls, but don’t expect marriage or sometimes even monogamy. But don’t we as guys do this as well?
The next category is what you’re looking for if you want a serious GF in your 30s.
4) The Normal Girl. Believe it or not, regular women do make it to their 30s without drama and head issues. They do want to date you and have fun and eventually meet the right guy and get married. Unfortunately you’ll have to wade through the rest of the women until you find one like this. But if you know yourself really well (and, therefore, know what you’re really looking for in someone else) then it becomes easy to weed out the bad ones AND recognize when you’ve found one worth keeping around.
Good luck man and have fun.
Yeah, I was ranting last night. I had just got back from happy hour and I was at my breaking point in regards to dating. My experience has been the complete opposite than what you’re posting. Hooking up in my 20s was way easier than it is now. I’m 34. Maybe living in a town that has a population of only 12,000 people and it being the middle of winter has something to do with it, but around here you hardly see single, attractive women in their 30s. Opportunities are far few and in between. I’m sure a big city like San Fran might be a different story. I don’t know how to increase my chances of hooking up and it sucks!
As far as seducing the woman, I really meant trying to have sex with her that same day/night you meet her. I’ll see these younger dudes flirt and flirt and when the girl leaves I’ll over hear them saying: “Why didn’t she go home with me?” and I’m saying to myself it’s because you didn’t get her alone. Hey, I maybe old and lame now but I did have success at one time, lol!
Dating, as far as opportunities, are definitely different in the city compared to, say, someone’s small hometown. Add into the equation the fact that who you pickup, date or hang out with in a small town has an extra layer of “small town gossip” added into it. So it’s kind of like there is this added obstacle; not only do you have to charm her and her friends there in the moment at the bar, but also make sure that all the little people whispering in her ear are content as well. Sounds complicated and daunting.
Luckily, if you’re looking to hook up with girls the same night I think you can step back and look at it from a logistical perspective. If I were single and in a small town (with no way to leave and go to a town with more options, since that would be option #1) I would get an apartment within walking distance of the bar scene, no roommates. This would make it easiest to plan out an afterparty. Also, I get the impression that you are trying to separate a woman from her friends in order to get her home with you. That’s cool, nothing wrong with it at all. But if it’s just not working for you you can also try other things, like the above-mentioned afterparty where you bring the whole group back to your place. If you don’t have a condensed bar scene try a rolling bar. But these are just a few ideas, and I hope that maybe they will spark some creative ideas of your own that can increase your chances.
You know, I never even thought of the whole gossip thing! Interesting point. Luckily, my house is within walking distance of the bars. This is an added bonus in the summer time. Opportunities do present themeselves, however just not as often and I guess it’s difficult to “get into a groove”
I’m going to start hanging more with the happy hour crowd as that seems to attracts all sorts of age groups, especially the older 20s – 40s group.
Hey Johnny, I’m sure it can get challenging in a small town like that. I used to be at my wit’s end just living in San Jose.
Being single in SF is a lot more fun. I’m glad you’re looking at some alternatives to change things up.
Hey Rob & GK,
I thought this article was relevant to me because things recently ended between me and a girl. It was hardly a serious relationship — we were only seeing each other sporadically and it was mostly physical. Nonetheless, I felt a little hurt that it ended because I really would’ve liked things to have gone further.
Now that I’m back at square one, here’s my game plan. I’m going to focus more on meeting girls through mutual-interest groups and not so much on trying to strike up conversations with girls in bars/clubs.
Maybe I’m going to take some heat for saying this, but NYC is a very difficult place for a lot of guys to meet girls when it comes to the night scene. For most guys who don’t regularly go to bars, I don’t think they’ll have much success in meeting girls at bars because they won’t be having fun. They’ll be working, which is not attractive as you pointed out. Plus, a lot of really good-looking and cool girls don’t even regularly hang out at bars, you know? It took me some time to realize this, but the kinds of girls that are a good fit for my personality do not go to bars regularly. They tend to spend Friday and Saturday nights doing things like going out to dinner with a friend or watching a movie at home.
In terms of putting my ideas into action, I attended a volunteer event through New York Cares on Saturday. There were slightly more girls than guys. I had a fun time (although I did get sneezed on a lot by a kid I was looking after ha ha). I didn’t really meet any girls I was into, though, which is no big deal in my opinion.
I could be wrong, but my guess is that a lot of girls sign up for things like meetup.com or New York Cares to find a date. I plan on signing up for events that genuinely interest me and I’ll only go to events that I think I’d have a good time at, even if only guys showed up. Pickup will only be a secondary concern. I’m curious, though, have you ever dated girls you met in meetup groups or mutual-interest activities, or even in something like speed dating? I’d love to hear your experience in meeting girls at those kinds of events.
Also, in full disclosure, I’m no expert at dating. I’m in my mid-twenties and I have significantly less experience with girls for someone my age. So anyone reading this should take my ideas with a grain of salt. That said, I think I do have enough experience with dating and girls to have a better idea of where I should be looking.
Yo Sal, I hear what you’re saying about the NYC night scene. I personally really enjoyed going out at night to meet girls as opposed to during the day, but that’s also because I wasn’t looking for anything serious, and I think the night scene is great for that. On the other hand, I have a good friend who just wanted a girlfriend, someone to get close to and hang out with on rainy Sundays and all that stuff, and he hated the NY nightlife because it didin’t seem to attract that type of girl for him.
So if you don’t like going out and don’t like the type of girls you meet there, then you are 100% on the right track to join meetup groups. This is probably already something you’ve thought about but I would also add that you should plan ahead for what you will do after the meetup group is over. I just browsed the meetup.com listing for Manhattan and some local food co-ops are sponsoring events. So lets say that you go to something like that and tour a whole foods or something and learn when an avocado is best (it’s when it’s soft). Now it’s 4PM on a Saturday, what do you do? You could go back home, or you could suggest to the 20 people or so in the group that you go to the bar around the corner for a round.
So for speed dating, I’ve sat in on events kind of like moral support for friends before but have not participated in one myself. It seemed like girls came in twos, one actually looking for a guy and the other also as moral support. I like the idea of dating for just a few minutes and then moving on, but I watched some guys screw it up by either being too serious or not serious enough. The ones that were too serious came off as stiff and desperate, the ones that weren’t serious enough, well, the women actually looking for a guy kind of wrote them off. In my opinion the best thing about speed dating events occurs about 30 minutes after the event when everybody stops by the bar for a drink. That is when I would jump in start talking and see if you could extend the night a bit. Like the meetup.com idea, there’s always the issue of “what happens next.”
Girls definitely do go to meetup events to meet guys. I attended a “business networking seminar” with a buddy at a little underground place during happy hour in the middle of the week. Put all that together and I was planning on it being super lame. Turns out I was wrong. I hooked up with a chick in the back room, my buddy took a girl on an instant date afterwards and then, as I was getting off the subway to go home I saw another girl I had met at the “networking event” and got her number too. So yeah, I endorse them. However, I think it would be easy to come off as “that guy” if all you did was chase tail at something like that.
One more thing, if you just want something to do during your free time then pick any meetup group that interests you. However, if you are really, in the back of your mind, looking for a girl, then avoid meetup groups that are girl-repellant, like tech groups. I know its obvious but I just wanted to throw it out there. In my opinion, the absolute best way to meet a girl that’s girlfriend material without going out to the bar is to get to know people who like to throw house parties. House parties will attract all the girls that like to stay home on weekends, just the type you’re looking for.
I just thought I’d add my two cents for Sal. I’ve done speed dating once, but it was for a documentary, which probably changes the dynamic. But after watching some wanna-be PUA guys do it badly, I would definitely put the emphasis on fun while being as genuine as possible — no bragging, no posturing, no serious questions. Make sure you’re sober. And of course, since your time is brief, look your best.
As for meetups, I wasn’t impressed with the one event for 30-somethings that I went to in SF. People there were a little off socially and the girls didn’t look good. But it may be totally different in NY. Rob’s advice is excellent.
What I have been impressed with, however, are the nighttime museum events we have in SF. I’ve seen lots of high-quality women at those things. I’m sure the Met or some place like that throws similar events in NY.
Also, for finding a girlfriend, you may also consider the online route. It’s not my preference, but other guys speak of it highly. Two of my cousins found their wives that way.
Thanks for the advice guys, here’s how I’ll try and incorporate it.
Rob, I’m glad you mentioned the “what to do next” because I usually do have free time after meetup events. Instead of going home, I’ll try and extend things a little bit and get some peeps together to hang out afterwords. 99% of the time I don’t ask people to hang out afterwords, mainly because it’s the path of least resistance. Now I’ll actually make it a conscious goal. Also, I like the advice on house parties. I’ve got a good a friend of mine who invites me to stuff like house parties and trips to AC — he’s the kind of guy who makes friends with everyone and at least once a month he knows of something fun going down. What’s even better is he’s willing to freely share that info, and he invites me to that kind of stuff. Coincidentally, I’m hanging out with him tomorrow (assuming it doesn’t snow too badly and I can’t drive out to see him), and I’ll ask if he knows of any fun parties coming up.
GK — I think you’re on to something good with the museum idea. By the way, you guys in San Fran are spoiled with having such a good night-time museum scene. In the summer, I got a chance to visit SF and I took up your idea of hitting up NightLife at the California Academy of Sciences with my friends. We ended up having a blast there, and the place is teeming with beautiful women. I’ll look into what NYC has going on with museum events.
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