How to Find Your Dating Groove as an Older Millennial

How to Find Your Dating Groove as an Older Millennial

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Once upon a time, Saturday night was Date Night.

Now, for older millennials, Saturday night is:

  • Self-Care Night
  • Catching Up on Work Night
  • Netflix Night
  • Instagram Story About Anything But a Date Night

What happened? Oh, I can wait to date, we think. What the heck are we waiting for? We are hyper into everything else but pursuing a relationship, yet want a spouse before 50. We want it all, with a mate on the side (hold the baggage please). By we, I mean me. I didn’t want to worry about it, then I really started worrying about it. That was last year.

Approaching 39, I made marriage the mission. “Put a ring on it-we’re going to the chapel and we’re gonna get ma-a-a-rried-as we walk down this aisle together,” became my motivational mashup. Alas, I needed to go on a date, many dates, all the dates. Aaargh (insert side-eye emoji).

Dry spells can hit at any age, but Dateless Millennials: The Parched 30’s & 40s, is the newest phenomenon sweeping the globe. I had to end a three year drought. The thirst became everything. I reached a critical point of over-thinking and under-doing. It was time to get real and get it into gear. Here is what a year of confronting the dry, harsh truth looks like.

April 2018

  • I started going to Catholic things, all of them. I started going to all the talks, singles mingles, prayer services, concerts and bible studies I could. Not caring if events were tailored for me, as an older millennial, was critical. If I was the only “YA” over 30, oh well. Some events were corny, some were cringeworthy, but more than expected were soul-lifting and fruit-bearing. At an art event, I exchanged numbers with a handsome young graphic designer, yet I could have stayed home and done absolutely nada and talked to nobody.

September 2018

  • I started staying for Coffee & Donuts, Wine & Cheese, or whatever. At first I was hesitant to attend these parish events, having no reason not to beyond fear of social awkwardness. I’ve gone, chatted, sipped, nibbled and felt all the better for being part of the community.

October 2018

  • Bars are not the big bad. I had an interesting bar night with a friend. We ended up talking to two respectful, funny and intelligent gentlemen. Those were two intriguing male conversations more than I had in all day. I was reminded that prize men are paying attention.

November 2018

  • I joined Catholic Match.
  • I leaned out. How very millennial of me to peace out of my profession. Approaching my 40’s, I’m not going to find a husband adding daily overtime, eating desk lunches and being too tired every weekend to even think about a date (one I may be cranky or thinking about deadlines on). I changed career direction to goals that allow freedom to find someone, said sayonara, and never looked back.

January 2019

  • I just got over myself and went on a date already. I challenged myself to put aside pickiness, ego, reservations and just accept a date already.
  • Social side hustles and volunteering. To decrease spending and increase activity, I began work-study at a boutique fitness studio. I also started two volunteering assignments to build my skill set and interact with the public. Engaging with a rotating array of individuals can only add to my chances of making a match.
  • I decided to start transforming what I didn’t like about my physical, mental and spiritual self and accept the rest. The end.

February 2019

  • I didn’t move. After 16 lonely years as a Brooklynite, I contemplated moving somewhere quieter, cheaper and with a less “me, me, me” mentality. Reading so many of my cohort on CatholicMatch lamenting limited population and social resources, I realized what NYC has to offer singles. Staying in a city with a large Catholic headcount, in a thriving metropolis, along with focused determination, can only help me land a husband. I could still end up in a toned down town, but it would be a collab with my mate.

March 2019

  • Age ain’t nothin’ but a number, sort of. I recently accepted dates with one men nine years younger and 14 years older. Five, plus or minus, is my ideal. I’m still not 100% comfortable with pushing the age bracket, but I’m softening.
  • Help! A brother at my parish leads the 25-39 year old men’s group. I made sure he knew I’m available and his eyes and insights would be appreciated. I have no shame in my game.
  •  I’m not “settled”... and? I’m not totally financially secure, established in my career or a saint, but I will never be perfect, nor will he be when we meet. There is no perfect time, so the time to is now.

Stats from the last year

  • 1 date completed
  • 1 date to come
  • Several interested men
  • Confidence restored
  • Prospects abound

Conclusion:

To marry, you have to date (shocker), to date you have to make moves, to make moves you need to dust yourself off and try again, shake it off, whatever you wanna sing to yourself to get the party started.

I am not yet engaged, but I have been engaging and am better off than I was a year ago (results above zero). The moral of my story is live fast, try young and and banish the dry spell (a.k.a. get out there and get over yourself).

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