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Dating was not top of mind.

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However, for both newbies and longtime singles, there are skills, strategies, tips and techniques that can help ease what can be an awkward experience. Before online dating was popular, Maureen Callahan, a resident of the Twin Cities area dating in midlife Minnesota, had a year career connecting singles.

Starting in the early 90s, she worked for a video dating service; the business brought singles to an office to review short clips of prospective matches. Both sold memberships in a club that staged events, activities and outings for singles looking to have fun and expand their circle in the quest for friendship and romance. While the methods for searching for a spark have changed, what the two learned about dating remains relevant to both of them as singles today. Jeff, 54, now a Realtor, has enjoyed several serious relationships but never married.


Maureen, 55, a teacher, is circulating again following a divorce a few years ago. As part of our "Dating After 50" series, the friends sat down with Next Avenue contributor Kevyn Burger for a frank conversation about midlife dating. Maureen : I remember when online dating started; there was a stigma associated with it. Now everyone and their kids are on the dating apps. The dating sites are a target-rich environment.

The midlife dating crisis

The more people you have exposure to, the more luck you can have. There are many ways to meet other single people but you have to want it; you have to want to be in a relationship. Maureen: I shy away from the free dating sites.

I argued that side of it in the dating industry; you get what you pay for.

The truth about midlife dating and sex

Paying for a membership bleeds out the scammers. On free sites, they have nothing to lose. You can weed through the BS more quickly.


I see people online who say they want companionship. With chemistry, I now give guys a little more time. They would say, 'I don't know if I can date you;' they had teens and tweens and wondered if I would understand their lives.


Dating over 50 has been much easier than it was in my 40s. Now women date me because they want to. Guys, you have got to write something. Don't do that. Asking up front makes my skin crawl. Jeff: Match. Keep a little mystery alive. Maureen: Show me pictures of you, not your toys or your dog or your lake cabin. Jeff: When I meet someone dating in midlife, I spend a little time on the phone to dating in midlife out if we have any common interests and common values.

I want to hear how they express themselves. Being a bachelor, I eat out a lot, so I like going out to dinner. If I meet someone for coffee, I can find nine reasons to weed them out in that quick fifteen-minute coffee date. Over dinner, when you spend an hour, you have time to get to know them a little. Keep it light and fun. I like to go out for a glass of wine and I like the evenings — the lighting is better Laughs. Jeff : Working in the dating industry, I saw singles make connections and find a new life. They were coming to us because they were busy and looking for assistance. They didn't have a large pool of single friends and they were looking for a place to do something different that was safe and fun.

Now with online dating, I think, maybe you will make a new friend. Maybe they will connect you with a new circle and you will meet someone through that. I feel safe [at that bar]. If anything didn't pass the 'tummy test,' I could excuse myself, go to the bathroom and get out.

The dating game: looking for love in midlife and beyond

Jeff : People you meet online are strangers. I tell women to use their middle name; some women put out too much information too soon. With a first and last name, [someone] can find out where you live and other information; they can put it in Facebook and see pictures.

Men have to think about safety issues, too. Online, I use the city I work in, not the city where I live. The worst thing that has happened is I have dating in midlife for some false advertising. I don't want to be the experiment or the teacher on transitioning to being single. Maureen : Most people I meet are divorced and I ask about the marriage pretty early on.

It says something if someone is not connected to their family.


I didn't wait this long for someone who is not the right fit. Search Search. Health All Health. The Coronavirus Pandemic. America's Entrepreneurs. All Living. Telling Our Stories. All Caregiving. The Future of Elder Care. X Search. Free vs. Paid Dating Sites. Kevyn Burger is a freelance feature writer and broadcast producer.


Based in Minneapolis, Kevyn is the mother of three young adults and one rescue terrier. Meeting the needs and unleashing the potential of older Americans through media.


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