Dating as an older woman: "I found many men my age, but usually, the younger men were more interested" 

The rules of the dating game have changed. What was earlier considered rude might now be considered expected honesty. Who pays is still up for debate, and the overlap between dating culture and hook-up culture has many of us feeling like a pomfret trying to blend into a school of goldfish.

Stepping into the world of modern dating can be incredibly intimidating, especially when you’re coming back after exiting a long-term relationship.

Deeksha Kapoor*, 50, didn’t know her left swipe from her right when her friend signed her up for Tinder. The Bengaluru-based kidswear designer had no idea on how to navigate these unchartered waters going into dating as an older woman but definitely didn’t expect such a bumpy ride.

Read her story about dating as an older woman and the real gift she received through her journey:

I was 39 years old when I separated from my husband. The whole experience was quite traumatic, so it took me a couple of years — counselling and a lot of soul-searching — to get back on my feet. Coming out of a terrifying experience like this, you suddenly want to relive parts of your life that you felt you’d given up on – just having fun and being young again. 

I was in my mid-40s when my friends started pushing me to get back into the scene. “Come on. It’s been too long. It’s time you started going out and meeting new people,” they’d say. I’ve always been a very social person, but meeting new people, namely men, hasn’t been easy. I run my own boutique, and given my line of work, it’s rare for a man to walk in to get clothes stitched for children. I’m also the kind of person who doesn’t really get noticed if I go out with a large group of people. I realised I was at a disadvantage when it came to organically meeting people in real life. So when you’re dating as an older woman, the apps make sense. 

I didn’t know Tinder from Grindr or Bumble. So I had a younger friend set up a profile for me, show me the whole swiping business and what happens when you match. She said, “You know, I have a lot of friends who have met their life partners on Tinder.”

Going into it, I was completely naive. I had met my former husband when I was 21 years old. A couple of decades pass by, and you have these doubts about yourself, who you are, and how you look—dating as an older woman is definitely intimidating. More so when you’ve gone through bitter experiences in your life. You tend to be a lot harder on yourself, questioning everything and everyone coming your way.  

Being in my mid-40s then, I found many men my age on the app. But for some reason, it was usually the younger men who were interested. 

I made the most of my texting skills and started conversations with people on the app. I slowly realised that many people wanted to go out with me. All the attention, compliments and flirtatious behaviour were such a morale booster. 

Let’s say I signed up for the account on a Thursday. I spent all day Friday talking to one particular man who was very enthusiastic about meeting me. It felt good. I had never put myself out there like this before. 

On the first date, I decided to pick a place that wasn’t very far away from my house. When I met him, it started off with a lot of compliments, and for me, that took a while to sink in. To allow myself to feel like this again. You close so many doors without realising because of everything you’ve gone through. However, the date was a disaster. 

He cribbed about the food and drinks, then insisted we should take it to another place. I asked him what he had in mind, and he said his place. It was so direct. I like a bit of tension, the flirtatious build-up and courtship. I didn’t even know how to react. When he started getting pushy, I became uncomfortable and said I’d like to go home only. So he called for the bill to wrap it up though I thought we’d still continue with our date – I was barely halfway through my second drink. 

After insisting on driving me home, then threatening to turn the car towards his place, I think I managed to confuse him enough to take the left turn needed to get to my building. I barely got out of the car before he drove off. 

Still trying to be polite, I got to my house and sent him a message, saying I didn’t get a chance to thank him properly for a wonderful time. Then I went to sleep. When I woke up, I saw that I had been blocked. 

I was disappointed but didn’t let it deter me. There was one week during which I met someone new every day. But each was more disappointing than the one before. I started to question the whole concept in my head. I thought, maybe I’m stuck somewhere in the past. I need to move on and evolve with the times. I wasn’t the kind of person who would jump into bed with anybody (not that there’s anything wrong with that if that’s what you prefer), but it’s not for me. But I realised that everybody I was meeting was pretty much taking it in that direction. 

Nobody wants to spend time getting to know you or even meet you a second time. If something intimate happens after the first meeting, then great. If it doesn’t, they couldn’t be bothered to try for a second or third meeting to even have a conversation of any kind.

Perhaps the sheer number of married men on such apps surprised me the most. Most of them don’t even make their relationship status known. I didn’t know that “Are you married or single?” would be a question you needed to ask someone. On a dating app, I’m assuming we’re all single. But I was wrong. 

Everyone talks about red flags nowadays. When I started dating as an older women, some things made my antenna goes up. Certain phrases, body language… my experience of being in an abusive marriage had taught me to watch out for the signs. Whenever someone has such a tingling sensation, listen to it, especially when you’ve had a bad experience in the past. It’s better to act on it, then. We tend to say, oh, it’s not important, then before you know it, you’re sucked into it, and it’s too late to get out easily.

My children are 18 and 20 years old. Through them, I’ve realised how to be more discerning in picking the people I want to surround myself with. The same way that they do. During the COVID-19 lockdown, I was doing a few virtual dates on video calls, and my daughter one day turned to me and said, “Mom, why do you alway laugh at their jokes when they’re not particularly funny?” I had never really thought about this. In my way, I was trying to be polite and make the other person feel comfortable.

My daughter said, “By not being yourself and laughing at their stupid jokes all the time, you’re showing them that the bare minimum works. Why do you downplay your own intelligence to make someone else feel better? Why are you always trying to make other people feel comfortable?” Her words have stuck with me. I see so much maturity in my children, which is lacking in the 40 and 50-year-old men I’ve met on these apps.

I’ve had a messy divorce. I watched my children fly the coop and go on to live their own lives. When I got onto these dating apps to try and find some company, I was unsure, apprehensive and filled with self-doubt. I don’t think these apps are meant for me. At least not what I’m looking for. I don’t think I’d get married again, but I will commit to a relationship. While dating as an older woman on these apps didn’t work, there has been a bright and shiny silver lining in this experience for me. 

I met a few people with whom I immediately hit it off. After the initial flirting and Whatsapp chatting, we realised that there was chemistry from both sides, but it’s a platonic bond of a great friendship in the making. 

I’ve met somebody who owns a cafe. We get along famously, though we live in different cities. We’re great friends now. I’ve met his kids; he’s met mine. I think you realise as you get older that while dating and romance is great fun, you want good friendships too. For me, what’s come out of this whole experience is a couple of great men who are now superb friends. 

Even through this maze, I’ve managed to make amazing friendships that have lasted longer than some marriages. Perhaps we’re at a point where we slowly realise that romantic relationships are overrated – good healthy friendships are what carry you through life. When you’re in your 50s, you really want to build your soul tribe. 

On my journey of dating as an older woman , I’ve gone from being a very insecure person to being confident and comfortable in my skin. I’ve evolved, and while the men I met on the dating apps may not have joined me in this journey of growth and introspection, I still have hope. I haven’t given up, and I’m ready for someone to prove me wrong. 

*Name changed upon contributor’s request for anonymity. This is a personal account, as told to Sara Hussain.