What To Know If You’re Over 50 And Online Dating

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dating tips over 40

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Singles 55 and over make up one of the smaller groups using online dating apps, but their activity is on the rise. If we consider the possible life circumstances of someone in these age groups, it’s wonderful that online dating is a tool available to them. A woman who is online dating in her 50s may have never married but be surrounded by friends who are busy with their marriage and family lives, or she may be divorced or widowed. Fifty years ago, a woman in any of those circumstances would just be rather isolated. It’s hard to move into new social circles in the second half of your life and meet other singles. It’s hard to put yourself out there after the trauma of something like a divorce or the death of a spouse. Online dating opens up a whole new world for this age group that wasn’t available as recently as a few decades ago.

All that being said, whole new worlds are pretty intimidating and become harder to explore as we get older. By the time someone reaches 50 and up, they’ve been working with certain ideas about relationships and communication for a while. Online dating can disrupt all of those ideas, and being successful on the apps can require change that feels like learning a whole new language. So even though singles in their 50s and beyond may benefit the most from online dating since they’re short on conventional methods of meeting people, they can also be the singles who struggle the most with it. We spoke with TextNow dating expert Damona Hoffman (pictured below) about how singles in their 50s and up can thrive in online dating, and some mistakes to avoid.

Damona Hoffman

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Women are naturally better at it

Hoffman discusses some of the reasons women may be naturally better at curating their profiles – even women new to online dating. “I work a lot with women in this age group to manage their expectations for what men are going to come to the table with. In our culture in general, women are taught more about grooming. That is more a part of our consciousness or upbringing,” she says. “Women over 50 have photos of themselves.  The men that I work with over 50 are not taking pictures of themselves and posting them on Facebook. Women are more groomed for presentation because it’s taught to us from a young age. So often with this age group I see women come in and say ‘Every profile from guys my age sucks.’”

dating tips over 40

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Try to look beyond the picture

Online dating is such a visual medium, so it can be difficult when you’re dating in a pool of men who don’t know how to create a visually appealing profile. The onus is a bit on women to see beyond what men put on their profiles, says Hoffman, even if it’s tough. “I have to remind them, those guys don’t have a dating coach. They don’t have people who are looking at their photos. They’re not conditioned to look at their profile in that way. The lion’s share of men’s profiles over 50 that I read are pretty much terrible. I have to get [my clients] to see the possibility, even if their pictures are not ideal.”

dating tips over 40

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Men present as providers

I told Hoffman about my experience helping a relative over 60 with his online dating profile. He’d put his first photo as his professional headshot – very serious, in a three-piece suit. It was a nice photo but not a fun photo. I couldn’t understand how he thought that was what women wanted to see. But Hoffman explained, “They don’t know how to describe themselves in terms of their personality and the things they offer in a relationship…outside the context of being a provider, etc. People over 50 have worked so hard to build their life and have their stuff. There is this feeling in dating where instead of showing ‘who I am’ it’s more about ‘this is what I have.’”

dating tips over 40

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What men look for is different

Let this spark all of the debates about gender roles, societal expectations, and misogyny that it will, but these are just the facts. While a lot of men in these older age groups think it’s their job to present what they can financially offer, those same men do not look at what women have. They’re more concerned with personality in regards to how a woman would be as a companion. Hoffman says, “That’s how men attract women but men are not interested in that. He’s interested in what you bring to the table. He doesn’t care about your stuff.  When you’re in your 50s, your social circle is pretty set. Your hobbies are set. You may have already had a family. You’re in a different phase of life that’s more experiential so I have to get people to lean into that.”

dating tips over 40

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Don’t assume he’s a cradle robber

If you often see men in this age group going for younger women, the attraction might be less superficial than you think, says Hoffman. She says that it’s a personality trait rather than a physical one that men like in younger women, but older women can have it, too. “A lot of women come to me in this age group thinking ‘All men my age want to date someone younger.’ That’s absolutely not the case in my work,” Hoffman says. “Men are attracted to flexibility more than specifically youth. They might go out with someone who is younger but if they’re in a different phase of life, they might not connect based on what they want to do. One person wants to retire and the other person wants to start a family.”

dating tips over 40

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You have to be open-minded

Dating past the age of 40 or 50 can be tricky because, at this age, you’ve lived a life filled with hard-learned lessons. You have wisdom. And some of that wisdom might have crystalized, making it hard to see the full picture with a potential partner. “Sometimes people over 50 will come to me a little bit rigid. They say ‘This is what my life looks like. I’m not willing to change anything to invite another person into it. This is my vision for a partner and they have to fit into this,'” Hoffman says. “It’s a much more fixed mindset than a growth and experiential mindset. Sometimes that is the thing I have to shift in people.”

dating tips over 40

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Watch where you draw the line

“I see a lot of people who say ‘I can’t date anyone who has younger kids.’ They say the kids must be out of the house. They must be launched. I find that sort of limiting,” Hoffman says. “I get it…as a parent…you dream of that day when they’re launched and off they go. And you don’t have to worry anymore about having food in the fridge for them and wondering what time they’re going to be home. I get the freedom that that empty nest brings. But at the same time, is that the line you really want to draw? If your perfect person has everything you want and had kids later and their kids are still at home, or because of COVID their older kids are moving home, is that really going to be the deal breaker?”

dating tips over 40

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How much does that trait really matter?

Hoffman really drives home the idea that it’s unfortunate we can decide that a certain trait won’t work for us before even meeting an individual. We can put more importance on something than necessary and could see how we would miss out if we actually engaged in a relationship with somebody. “People often come to me and say ‘I’m open to a life partner but will not marry again.’ I guess that’s a personal choice. But again if you meet the perfect person that you want to spend the rest of your life with, and they want marriage, is that where you’re going to draw the line in the sand?” Hoffman asks.

dating tips over 40

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Look at the whole picture

Is it wisdom or is it your prison? Hoffman says as a way of protecting ourselves, we might decide that any person who has a quality similar to someone who it didn’t work out with isn’t the one for us. “If we had experiences that went a certain way, we’ll make up a lesson from that. And we see anyone else who aligns with some part of that story as someone we cannot be with,” Hoffman says. “For example, it didn’t work with a Christian once. Or someone with kids once.  So now I will never date someone like that again. We make our box smaller and smaller. A lot of my work is getting people to take away the walls and see what really matters in the connection.”

dating tips over 40

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Let go of control

Hoffman speaks a bit to the power of being a bit less rigid in online dating here. “I’ve worked with women in their fifties, sixties, seventies, and even eighties. They had the experience of their lives once they approached things with flexibility and an openness to the experience,” she says. “Then they were desired again. That’s what I love about dating apps. Even 20 years ago, if a woman was divorced or widowed and over 50, she knew the people she knew and had the hobbies she had. How would she meet somebody? Now there is so much possibility. There are new ways to connect with someone that weren’t available a decade or two ago.”

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