I tried online dating as a widow in my 50s - here's what you need to know

Lady in off the shoulder denim top
Nicky Wake set up a dating app specifically for widows

My last husband Andy and I met online in 2002 on Dating Direct, so when I lost Andy in 2020 and was eventually ready to meet someone new, I wasn't a total novice when it came to online dating.

After a long period of shock and grief, I went back online and tried the mainstream dating apps; Tinder, Bumble and Hinge, and it felt like the Wild West. So much had changed in 20 years. I was dealing with ghosting and catfishing, and it was hard to navigate. I experienced plenty of scenarios that left me with battle scars.

Online dating in my fifties

Lady in off the shoulder denim top
Nicky Wake set up a dating app specifically for widows

Online dating is a challenge. At times it feels like a full-time job! You have to be proactive, you indeed get out what you put in. It’s also important that you are on the right apps. Unlike when I was younger, it’s now important to me that I date someone stable. I enjoy the flirting, the late-night banter, particularly as a solo parent.

It can be a minefield but there are some very sweet, nice and generous people out there. I have enjoyed it and have had some wonderful dates and short-lived relationships. I have made some wonderful friends and had two relationships. Neither worked out as I just wasn’t ready.

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I also had some trying times on the apps…

1. The married man

One of the first dating encounters I had was with a gorgeous man who had a job that meant he was forever in an airport travelling - similar to me at the time. We met in real life a few times and it appeared to be going very well. After a while, it dawned on me that we only ever spoke Monday - Friday, when he was travelling. He was, of course, married and returned to his family at the weekend. I cut off contact with him as soon as I found this out.

2. The close call

I got talking to a very attractive man on a dating app. He said he was a retired medical professional. He appeared quite young so I was surprised to hear he was retired but didn’t dwell on it too much. After a short time speaking on the dating app, he suggested we meet and moved our conversation to Whatsapp. His full name came up on WhatsApp and I googled him. The lead story was that he had been struck off for inappropriate behaviour with a patient. I now always google a date before meeting - nothing wrong with a bit of due diligence.

3. The missing spark

I met a guy on a dating app and he seemed so lovely, funny and sweet. We chatted for a week and then agreed to meet for lunch. We had absolutely nothing in common when we met, and had nothing to talk about. It was the longest lunch of my life. It taught me that the first date should always be a coffee date! Short and sweet.

The trouble with dating apps

I found traditional dating apps very difficult, so much had changed in the two decades I had been out of the dating world.

Us widows refer to non-widows as muggles and muggles sometimes find it hard to understand our situation. You see, death is so very different from divorce and it takes a very big person to date someone who is grieving the love of her life.

Andy’s memories will always be a huge part of my life, his photographs will always be on my wall. And that’s a lot for some people to take. With this in mind, I decided to create a dating app specifically for widows.

Man and woman smiling in australia
Nicky's husband Andy passed away in 2020

Changing the game

Widows and widowers are uniquely placed to understand each other, and their situation. The moment that I decided to set up an app specifically for widows and widowers was when I was ending a relationship I had with a man called John.

I explained to him that I couldn’t continue the relationship as I wasn’t in the right place, I was still grieving. He asked, “You’re still grieving?” He was shocked. I explained to him that I would always be grieving, I lost the greatest love of my life.

Non-widows haven’t been through it, so they don’t understand. On so many occasions people I've been dating feel threatened by Andy. But he’s not coming back!

Being widowed is so very different from divorce. You have a choice when getting divorced, even if one partner wants it and one doesn’t there still is choice involved, situations can change. But when a partner dies you cannot make any change.

After my experience with John, it dawned on me that I needed to create a safe space for widows and widowers to explore dating again. I feel like we’re solving a unique problem.

READ: 5 ways to support a loved one through bereavement

Introducing Chapter 2

I set up an online dating app specifically for widows and widowers, named Chapter 2.

Chapter 2 profiles are more detailed than most dating apps, they tell a lot more than on other dating apps such as how recently someone was widowed.

Widows, in general, are more open to sharing. Chapter 2 is a phrase extensively used within the widow community and is used to describe friendship, companionship, dating or physical comfort.

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The app provides a safe space for widows and widowers who are looking to find happiness once again. Chapter 2 has a rigorous sign-up process to ensure the platform is used by genuine, like-minded widows who are kind and respectful.

We insist on genuine photos, it must be a photograph of you and not, for example, a landscape or an emoji. Each member also signs a code of conduct and promises to be honest, respectful and to treat others with respect.

My advice for dating in your fifties

1. Find the right app and put the time in

Make sure you are on the right app for you, for what you want out of it. You also need to put the time in. Think about what you want from it and on your dating apps be strict with your filters, know what you want, be clear about it and be comfortable with it! Set ground rules too, if you’re not comfortable with something - for example moving your conversation off the app - then don’t do it. Don’t be afraid to state what you want, take control and don’t feel pressured. And ultimately - enjoy it, there are some wonderful people out there.

DISCOVER: I totally changed my life in 30 days - here’s how

2. Be open-minded

Be brave, be bold, be proactive and be open-minded. You might think you have a type but you might not. Be honest and be truthful about who you are and what you want. It minimises waste of time - for the person you are interacting with online. On a more serious note, be careful, don’t give away any personal data. If you do decide to progress and meet in real life, always tell a friend where you are and meet in a public place.

Dating as a widow

There’s no such thing as the right time when it comes to finding love again, it’s what’s right for you. But you need to be mindful of how children or in laws might see this. Their timelines might be different from yours. But remember, you are entitled to feel joy again, your partner would want you to feel happiness again. It can be very scary but here at Chapter 2, we are there to hold your hand through all of this. We can offer advice on how to navigate this new world.

Find out more about Chapter 2 and visit HELLO!'s Happiness Hub for more inspiring stories