Article: Dating in Your 30s: Why You Should Date “More than One” to Find “The One”

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Advice / Essays / essays and shorts / published / Thoughts / Uncategorized / Writing

An article I wrote for the guys over at Talk Thirty To Me on the benefits – no wait, NECESSITY – of casual dating in your 30s. Have a read and definitely a listen to Turg and RandyZ talk love, life, and nipple stickers ( * )( * )

It’s widely known that millennials and generations younger are getting married later. The reasons have been speculated all over the internet – abundance of options, focus on career, Tinder, etc. While there is a population that would rather wear their bachelor/bachelorette status over a wedding ring, many still are looking for “the one.” Whether you believe in a single soulmate or in multiple life partner possibilities, you’re still trying to find someone out of everyone who is compatible with you – a needle in a Tinderstack.

Throughout my 20s, I had a few serious boyfriends, but never really dated casually. After a breakup at age 30 and some much needed single-time, I was ready for a relationship. Getting back out there proved to be a harsh experience. It wasn’t all Nancy Meyer kitchens and Eat, Pray, Love. I found myself over-committed to guys who had no interest in being a couple. Frustrated, I retreated back to singledom and self-reflection, but emerged with a new take on dating.

I promised myself I would date more than one person at a time, even though it appeared to go against wanting a monogamous relationship in the end.

What did I have to lose anyway? A few hours and possibly a few bad dates? Turns out, with this shift in perspective, I had everything to gain and here’s why.

Casual dating allows for a natural vetting process

By the time you reach your 30s, you know yourself better than you did in your 20s. This means you know more of what you want in a partner and chances are these are more substantial qualities – similar values, character, and compatibility. In your 20s, you’re more likely to date based on physical attraction (or ounces of alcohol consumed). The catch is

Deeper qualities reveal themselves over time

and don’t hit you over the head as immediately as lust.

Consistency is a very important trait for me and it was only by dating 3-4 guys at once that I got to comfortably see who put in regular effort to see me. I got to actively compare one man’s level of consistency against another. We comparison shop for appliances and phones. Why wouldn’t we for love? The reason this was most comfortable for me was because …

Casual dating spreads out the anxiety

I’m an anxious person anyway. It’s why I hate roller coasters and anything that implies free falling. Like many other women, when I approached 30 I felt pressure to “settle down.” Suddenly, every date had to have “potential.” Every relationship had to result in marriage. Approaching anything with that level of expectation is bound to result in disappointment. Dating around spread around my anxiety so to speak. I was never waiting around for some guy to text me back because I was talking to several. By not putting all my proverbial eggs in one basket, I was able to relax and have fun – which is the best part of dating! Most importantly, my mind remained calm and objective – key mental states for getting to know someone on a deeper level and seeing if potential for something more serious is there.

Casual dating = Accurate commitment level

A lot of advice for women says to date casually because “that’s what he’s doing anyway.” I don’t ascribe to adjusting one’s behavior based on another cause what if their behavior sucks? His commitment level may not match yours, but that doesn’t mean you should stoop or rise to it. Ultimately, you need to do what’s best for YOU and rather, act authentically to THE OTHER COMMITMENTS IN YOUR LIFE.

In your 30s, it’s probable you’ve cultivated deep friendships, invested in your career, and have a few hobbies. Pair that with the stress of ageing family, maintaining your health, what is a 401K? – and your time is stretched pretty thin.

I experienced the biggest burn out of my life in my early 30s. With a bout of depression and a failed startup under my belt, I knew I wanted to date, but wasn’t sure I had the time and energy to devote to another person. It turned out that dating casually – a couple of short dates a week – was better for my schedule and sanity. Coffee, cocktails, and concerts were a reprieve from my daily responsibilities, rather than a means to marriage. (I’ll talk more about how to casually date effectively in a future article – if Randy and Turg will have me). The company of men went from stressful to joyful when I changed my point of view and learned to juggle multiple dating partners.

On the surface, I can see why seeing several men seems contradictory to exclusivity. As someone who is more familiar with monogamy, my depth as a person grew by looking at my past, wanting a different future, and having the courage to take a different approach. Yes, it was a tricky game of trial and error, but it came with the deep realization that there are many paths to a single destination. And if you let yourself be open to them, you just might have fun along the way.


  1. I love this post. It’s so true – we are so much more aware of ourselves and what we want and how to start and deal with a healthy relationship. Sometimes even when we are younger we see something healthy and run from it. Even if we DID find “the one” when we are in our 20’s we most likely wouldn’t make it work the correct way. Casual dating in my 30’s (I’m only 31 now, though) has been amazing. I don’t waste time, I don’t think I’m in love in 30 seconds and I am on my way to finding the person that will enhance my life and that I can also give value to. Thanks for sharing your insight.

    Liked by 1 person

    • Hey Ryan, so glad you felt this one ! Best of luck to you … it sounds like you’ve lived some life and given some serious thought to what you want. Only good things from there (:

      Liked by 1 person

  2. A well written article. Makes a lot of sense too. You’re right author, I believe if one can ignore the pressure to settle down at all cost. One begins to see clearer and make better decisions. At this stage one now understands physical look shouldn’t be “the criteria” to date him or not. You made a valid point author-“give back to them at this stage what they give you.” After some casual dates, then focus on the partner that have the qualities you need and compatible with instead of carrying your heart on your sleeves.


  3. Great post. As someone who was never much of a “casual” dater, I think I missed out on a lot in my younger years. I wouldn’t go out with anyone unless I absolutely thought they were the cat’s pajamas. This lack of experience has made me a bit of a dunce in the dating department, I’m pretty much having to learn the things most women already knew by the time they were 22.

    Liked by 1 person

    • So glad you liked this and thank you for your comment ! I am in my 30s and can say it’s never too late to learn the lessons you “should have” learned in your 20s. In fact, I would argue that casual dating has been a better experience for me at this age because I’m more comfortable in my skin – leaving more room to relax, have fun, and find someone truly compatible. I’m not sure of your age, but I would guess that if you’re older, your self-awareness and wisdom only increases. So much LOVE to you and keep me posted on how things are going !!

      Liked by 2 people

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