The Pitfalls of Dating After 30


Everyone wants to know the key to dating successfully once you cross into your thirties, aka Thirtyville. Thirtyville represents more than an age. It’s a time in our lives when we’re expected to have more clarity,  greater stability, and a deeper sense of self. Our thirties are the manifestation of all the growing, building, and learning we [supposedly] did in our twenties. We should reap benefits of sowed seeds and have everything fall together nicely in our lives. But so often that fails to be the case. Most of us are dissatisfied with our careers, having chosen bigger paychecks over passion and purpose. Meanwhile, many remain actively engaged in the dating game wondering when and if we’ll ever find The One (or at least someone worthy of the title ‘Runner Up‘).

So what’s the real deal with Thirtyville? Why isn’t it akin to a promised land of milk & honey? Why are we still struggling to answer questions thrown at us a decade ago? While I don’t know everything about dating, I know a few things. Some were conceived from disappointments and poor decision-making, while others were born from investigation and introspection. Nevertheless, here are 3 major reasons we struggle with dating on this side of the bridge.

1) Increasing & Diverging Expectations. You know those ‘basic’ things you assumed every guy knew? Well here’s the secret. Those things aren’t basic anymore. Days of gentlemen opening doors, paying checks, picking you up on time (if they pick you up at all), or bringing flowers is a remnant of the past. There’s a noticeable push-pull dynamic in Thirtyville dating. By this age, most women have had at least one guy treat her fairly well and demonstrate what’s possible. And as the saying goes, “once you’ve been treated right, it’s hard to go back to bull–.” On the other hand, guys have spent years paying for flowers, food, and gifts only to find themselves still wondering if a woman deserving of their best actually exists. As a result of their own disappointment and feelings of resources wasted, men have pulled back. Some appear outright lazy in matters of love. So while women are expecting more, guys are offering less. Therein lies the conundrum.

“Expectations from your yesterdays may compromise a relationship meant for your tomorrows”

2) Accomplishments–Yours & Theirs. Regardless of gender, once you reach a certain level of personal success, it’s natural to become more discriminating in dating. Women feel more entitled to certain things because of who they are, what they have’ve done, and how they’ve done it (Marketing Vice President at age 35). Successful men find it easy to simply walk away when what a woman offers isn’t aligned with their ideal. Why should anyone have to compromise?  It’s another example of the ever-present push-pull.

If we crossed into Thirtyville having achieved the aforementioned accomplishments, we assume all age-appropriate suitors have done the same. When a woman finds herself owning, making, and running things – watch out. We get used to our world – our house, our rules, our life, and our definitions of right & wrong. So when a man comes along and isn’t where we believe he should be, we’ll never see him as an equal, let alone head of [our] household. We tend to fault him for not having the same boxes checked as we do because in our minds, not having what we have means he didn’t do things the ‘right’ way.

3. Baggage, Baggage, Baggage. We’re all walking around cloaked in the lessons of our pasts. Different relationships taught us different (sometimes the same) ones. We’ve learned, forgotten, and re-learned things that while nicely organized and captured in dating books, could never be mastered. Now, we unknowingly have layers upon layers of “life” around us and on top of us. Every opinion, assumption, judgment is the result of some event in days or years prior. So it’s clear to see how this makes dating in our thirties more difficult. When we interact with a romantic interest, we’re not merely interacting as two people. We’re interacting as two experiences-two lifetimes-of broken promises, regrets, distrust, fear, or whatever it is that weighs you down. The more years you participate in the sport of dating, the more baggage you accumulate. While our twenties may not have been the easiest time, we had fewer experiences and therefore, less baggage. Ironically, we expect more clarity and stability in Thirtyville yet never consider how ‘tainted’ we’ve become.

What do you think of 30-something dating and the expectations conundrum? Share your comments & Join the discussion!

If you enjoyed this post, you might also like “4 Reasons We Date Projects

Read, Like, Follow, Share! 

This post was originally shared on March 1, 2014.