So you?ve turned 40 and daunting as it is you’re also living in New York, the city of all cities. On top of that, you?re single and dating. Yay. Not exactly how you planned it, right? You’re living in the best city in the world and as a woman in your sexual prime, you should be jumping for joy but all of a sudden you are overwhelmed with feelings of loneliness and maybe even failure.

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It feels so bad….but why?

Well, it?s shows like ?Friends? that remind you to look for that old best friend you so desperately asked to be your spousal back up, only to find they?re already married. But that was in the nineties.

We?re in a new age now, right? Who cares?

Nowadays we have apps that allow you to find a date every night if you wanted to!

But is that what we really want? Is that what I really want?

Dating in New York is a different beast, at least for me anyway. I really believed that with all the magic of New York, there was still hope in meeting someone spontaneously.

Sure….if you?re at a gay dance party and you?re the only heterosexually charged female there with no one attending except the bartender and gay DJ.

I had to surrender to the fact that hearing those magical stories of how people meet are now limited to “we met on Tinder/Bumble/OkC/Hinge.? But you know what, there?s actually nothing wrong with that!

Dating options in NYC.

Aside from going to parties and hoping your coupled friends have single friends, or waiting in the subway and hoping ?the one? just happens to make eye contact with you and sweeps you off your feet (which could also be creepy), are there other avenues of meeting ?the one??

Should we accept that online dating apps are the way to go?

Dating in New York

It’s not impossible meeting someone in person, like during a downward dog position (get your mind out of the gutter! I meant during a yoga class), during a workout at the gym, joining weekend sports teams, running clubs, or meet-ups of any kind.

But in reality as New Yorkers, do you really end up talking to someone after a class and then have the courage to ask them on a date?

In this age of social media, people no longer know how to interact in real life, let alone spontaneously ask someone on a date! That?s why bars are hardly relevant for any kind of unbridled date proposals (unless of course they?re drunk…so there?s still hope for bars).

There?s also speed-dating which I think would either be fun or absolute torture. You?d either be talking over each other in a rush to finish a sentence or you?d both awkwardly sit there in painful silence with nothing to say.

In my opinion, in the end the most convenient way and now, most conventional way to meet someone, is through an online dating app.

Dating Apps – 40s Style.

For two years I refused to download any online dating app.

I hated the small talk and ice-breaking over texting. For me, the small talk never led to anything other than horny guys asking you inappropriate questions. I know that the dating app world had evolved two years later, particularly with all the safety measures.

Still, it became more of a “who swiped” or “liked” you and how many you got that day. I was more entertained by how bad people?s profile pictures were. Selfies in dirty bathrooms or even worse, professional boudoir shots!?

Eventually, I surrendered to downloading OkCupid. I wanted to avoid Tinder since it was notorious for engaging mostly in quick hook-ups. I was looking for something more substantial, but what I discovered was that ?the grass is always greener? notion got in the way.

It was more about ego than dating. People liked or swiped right, then didn?t have the balls to follow through with a normal phone call, which still happens today. That may sound seriously jaded and I guess I?m guilty of that too.

I could complain all I liked about the dating app scene but ultimately, I wanted to find a connection. For me, I think it?s more of a generational thing. All the rules have changed. Millennials were born swiping and liking and I had to learn and join them.

New York Men.

After falling off the edge of the dating app world, I dove right back to my familiar booty call, who happened to be a millennial, with no possible long term relationship in sight. I realized this is not what I wanted anymore and I deserved better. We all do.

Fast forward to Hinge two years later, I?m now a pro at this. Basically, because I don?t have to swipe at all.

After dumping my millennial booty caller, I was determined to meet someone new, or at least just go on a date instead of jumping in an Uber at 3 am and into someone else?s bed. I?m also in a different state of mind, not so jaded and somewhat happier with myself. Letting go of bad habits made life so much lighter.

After spending a few glorious weeks in Spain and Portugal, I felt revitalized and refreshed. Travel and vacation can do wonders! I was ready to get back on the dating wagon and getting on to Hinge was literally next on my to-do list. I remember hearing about it from my sister and staring at their subway ad ?Designed to be Deleted.?

I thought this was the app I was going to make my dating app come-back on. I had fresh, new pictures from my vacation to include and I loved the fact you didn?t have to write some cool reason why I?d be dateable and that I could be ?the potential one.?I really enjoyed the non-swiping feature, so as not to go through any PTSD from my OkCupid days.

My dating app comeback.

I accepted a date within a day of signing on. Our neighborhoods were close by so it was easy to accept and coordinate. I wasn?t nervous because I was only slightly attracted to his picture and wanted to get my feet wet. Kind of like a warm-up, a test run to see if I still had it.

I hadn?t been on a date in six months, (the last time was actually with a guy I met at the gay dance party I mentioned earlier on where I was the only heterosexually charged female in the house. The guy turned out to be married). And before that…wow I can?t even remember when my last date was. It could?ve been years. Mainly because I was falling for the millennial booty call I recently dumped.

Cougar datingSo my first Hinge date was a 38-year-old artist turned educational software app developer and Brazillian Ju Jitsu teacher.

The date went smoothly but there were no sparks for me. He called me out for calling him ?dude? which meant I was inadvertently putting him in the friend zone. Possibly true, though unintentional. After realizing he was my first online date in years, I received a rather telling lecture reflecting his current dating experience.

He said, to circle back to him after a couple of dates since I?d be experiencing terrible conversations during meals I really don?t want to have. I could smell jadedness in his advice. It was nice not to be the jaded one. I was the new kid on the block again.

Johnny, Being Catfished, and a new Millennial.

Being in my 40s I knew I?d come across a slew of divorced men all giddy and excited by the smorgasbord of women they could happily swipe through. One being Johnny, my second date. He was 53, tall, English and absolutely charming! It was such an amazing first date, that I actually started making a list of who?d I?d invite to our wedding.

There was chemistry, laughter, attraction and so much fun! At that time I was stupidly watching YouTube videos on how to date men and that I shouldn?t put them on a pedestal so they?d fall madly in love with me. Well, that backfired like a motherf**ker.

Johnny was so keen after our second date that he was frequently texting me like we were already together. But because of the ?no contact? advice from the french relationship expert I was watching, I ignored Johnny?s texts and answered them three hours later.

The Frenchman YouTuber guaranteed me a response and true love dammit!

Johnny petered off and I was back to the drawing board. To distract myself from the Johnny debacle, I accepted a date with another guy I was mildly attracted to. His stats showed he was 5?10 (a little on the short side for me, even though I?m only 5?2) but I was willing and able.

On my way to the 5’10 guy, I received a like. As I was sitting on the subway, I opened the app to find this absolutely beautiful, model-like guy liking one of my pictures. Before I could scroll any further his stats read 6ft 3, and…..27. As in years old!

I had to calculate how many years difference we had when I came to the conclusion that he was born just when I graduated from High School! I had to smile and playfully I typed ?thank you, David.?

Instantly he responded, ?for the like or when I held the door for you on the subway??

I looked up in shock and scanned through every door I crossed in my head. I was about to respond, but my subway stop for my date had appeared. I get off the subway all giddy over this gorgeous kid as I walked toward the bar to meet my date.

I was a little early and sat at the bar eager to text this David kid back. ?Wait..what? Where..I?m not sure if that was me though.?

It turned out he was just kidding. Still, I was so impressed with his creative ice-breaker that I was already hooked. I started texting a response only to be interrupted by my date who turned out to be shorter than my bar stool and no longer had the hair that was showing on his profile pic.Catfished dating

I was Catfished!

Needless to say that date was a two-drink maximum and I bounced. On the way home I continued to text David and a date was arranged before I got home.

You?re Not Alone.

All I can say is, being in your 40s, dating and living in New York, I?m learning to accept the things I can?t change. Dating apps are here to stay. I know that dating is a grind and especially in New York.

The city?s energy can amplify your loneliness. But the most important thing I realized is that I?m really NOT alone. I used to think I was the only single, 40-year-old in the entire city, but after a new perspective on life and scrolling through so many pictures, it dawned on me that I was definitely not the only one in my 40s, single and living in New York.

There was still the possibility of finding love and a connection regardless of whether it lasts or not. There?s always a chance one swipe or scroll away.

Oh and if you?re wondering how the date with the 27-year-old went..well I?m learning a lot about oat lattes and veganism. We?re still together…

K.D. Brighton

Author of – 40 SINGLE NYC: The Gold Notebook –?

For those of you that have been following our journey, K. D Brighton is a frequent contributor to Check out her other articles and feel free to have a look at her book with 5-star reviews, “40 single NYC; The Gold Notebook” now available on Amazon. is a participant in the Amazon Services LLC Associates Program, an affiliate advertising program designed to provide a means for sites to earn advertising fees by advertising and linking to As an Amazon Associate I earn from qualifying purchases.


10 thoughts on “What it’s really like being a 40 year old, single woman in NYC

  1. I love this site and I think it’s so great for older women to feel younger, and good about ourselves. It’s so important, yet so easily we dismiss people after their 30’s as just not as important. If youth is wasted on the young why not take it back when you hit 40?!

    1. Hey Sonia – thanks for stopping by and taking the time to comment. 100% agree with you! It seems like aging gracefully and classily is a dying art these days (plus it is tiring trying to compete with the likes of younger folks or thinking that we need to). I feel that it should come natural and we should feel great about ourselves at any age. Glad you enjoyed reading. I will be posting another article soon about “cougarism” haha 🙂 keep an eye out if you’re interested! Thanks again.

  2. Many thanks to you for sharing such a beautiful article with us and through this article I have learned about a very beautiful app. I’m actually 35 now and I’m a single woman but I’ve never used a dating app .But now I think I should try to get lonely and find a man for dating .The app you’ve mentioned has been using for a while .I hope anyone can use these apps if they like .

    1. Thank you Shanta. I am glad that you enjoyed reading and it resonated with you in some way. I truly wish you the best on your dating app journey! 🙂

  3. I also hated the idea of dating app (I’m 26). As you mentioned they’re full of of creeps who just want to hook up. I only had the app for a month I think before I gave up. I was lucky and met someone while in college thankfully! I think it is still possible to meet people “the old fashion way” but dating apps make it seem impossible (so we’ll use their service).

    I’m glad to hear your still with the 27 year old! Even if it doesn’t end up working out down the road I’d say don’t lose hope in meeting someone naturally. You never know 🙂

    1. Hey Sam. I appreciate your comments! And yes, you are right. I still keep my faith in the “old fashion way” of meeting someone. You are very fortunate to have done so and I wish you the best too. Thanks also for the words of encouragement!

  4. This is really an encouragement to older lady that they’re never alone. There is truly a possibility of finding love and a chance of someone coming your way. For sure, dating apps has come to stay. But the way it is now made it almost impossible to find your ideal man. But definitely, one will cross your way if patience sets in.

    Dating app is just not the only way though. It’s very possible to meet one when in gym, work place, restaurant, bar, just about anywhere. But combining them with dating app seems awesome.

    1. Hi Leon – I still believe (and probably prefer) the old school way of meeting people IRL but yes, you are right – adding the online dating app changes the game a bit and hopefully will help too! Thanks so much for taking the time to comment. Much appreciated 🙂

  5. Hi, Brighton.
    Thanks for sharing your experience of being forty years old and staying single in New York. The story was so touching and heartfelt. Being alone is a tough task and the thought of staying alone still haunts me. Now after going through all the ups and down in the article, I was so happy that you are in a perfect way now. Wishing you all the best wishes.
    Warm Regards,
    Gaurav Gaur

    1. Gaurav – thanks so much for stopping by and taking the time to comment. It’s a great encouragement. Thank you!

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