Rules for dating in your thirties

WHEN it comes to dating in your thirties, you've got to throw away the old rulebook and learn a new approach, writes AskMen's Mike Sheppard.

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WHEN it comes to dating in your thirties, you've got to throw away the old rulebook and learn a new approach, writes AskMen's Mike Sheppard.

What worked for guys in your twenties is probably not working for you now. In fact, what she used to see as your strengths have now become weaknesses. You need to turn your approach inside-out.

I had a great time in my early twenties. Not only did I somehow manage to date some really beautiful women, but I was blessed with a family that provided me with enough money in my pocket to do so with a little style.

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I’m not ashamed to admit that it helped my game since I was still reeling from ten years in an all-boys school and was trying to navigate my way through university. I wasn’t rocking the name brands just yet, but my jeans fit me well and I had a few shirts that looked good enough to walk into the right bars. School was the priority and work was part-time at best.

Dating was simpler then, even though at the time I felt like the world was being altered around every decision I made. Wrestling with limited responsibility while feeling overwhelmed was something that young men and women bonded over, and even formed relationships upon. We sat around and wondered about the future, griped about the present and distracted ourselves along the way. It was perfect fertile ground for meeting women.

When you’re in your twenties, everything is ahead of you. Bad decisions can be chocked up to youth, and consequences seem minimal - especially relevant when you’re heading into the field on assignment to meet a girl. These days, I have more considerations and second thoughts running through my mind when I’m on my way out for a night with the boys than I did on many first dates in my twenties.

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Most women had less subtly nuanced expectations for how a guy should present himself, but that wasn’t the only reason dating was more of a breeze. As guys, we were free to be easygoing optimists. The emphasis was more on being un-phased by the impending pressures, and less on looking like you had a perfect road map.

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Developing comfortable dialogue with women was all about being in the shared moment. There was something about that sense of discovery in life and mutual fear of the unknown that served as the best way to connect. Being in the moment was the ultimate way to make a girl notice you.

That was your twenties. Make no mistake, if you’re dating in your thirties, your circumstances have drastically changed. Your new circumstances are only recognisable in that they’re the complete opposite of what used to work.

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I’ve had two serious girlfriends and a lot of less-serious girlfriends in between. I’m pretty much certain that looking back, neither of them would date the guy that I was back then now that they’re in their thirties. In fact, I recall with stark clarity trying to impress an old girlfriend with a patented uni move of buying a round of shots, only to be met with a look of slight disappointment that I was still up to my old tricks.

Somewhere after being a student ends and being a man begins, we shift our focus. Suddenly, the guy who is still figuring things out at 30 feels more awkward than sought-after in dinner party conversation or casual bar banter.

If I am introduced to a woman at a party or at a bar through common friends, it takes only a couple of questions before we are onto what we do for a living. Just like that, my long-term prospects are on the table, and make no mistake, my prospects play into my attractiveness.

It’s not that women are looking for money, but at a certain point, security starts to look sexy. It’s not just women in their thirties who think so, either. It became fairly clear that the younger women were also drawn to this sense of security and degree of maturity. Can you blame them?

The cards we play have changed, and the strongest hand at the table in this new game has nothing to do with bluffing. You need to have something to show. It’s not about money (although that certainly makes things a little easier), but rather, it’s about conveying you have momentum.

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You can be the financial hero of the biggest firm, or an aspiring actor, but you need to make sure you’re sending out real passion or drive with some direction to boot. While in your twenties, you could sidle up next to a girl with little more than charisma to offer, the thirties require a little more of what was ultimately inconsequential back in the good ol’ days.

I know most of this boils down to confidence, and a lot of people will say, “Just go talk to women.” Ugh. Look. Not everyone is equipped to do that. And those who are already know most of this.

The point is that confidence comes from knowing where you are and what you bring to the table, and owning it. In your thirties, there is a larger palette to choose from as you mount your campaign to make your move. You may find yourself able to stand out in ways that were never an option in your twenties. You simply have more to work with. And, if you have a good grasp of what your strengths are when you’re out there, that leads to looking comfortable in your skin.

From where I am sitting, that’s just easier in your thirties.

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