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Entering the dating scene after just a few years off the market — let alone decades — can be an intimidating experience. Everyone else seems to have learned to send pictures on their cell phones, to write a quirky ad on and figure out how to upload flattering photos of themselves.

Nothing makes a woman feel out of the loop like technological advances.

A course might help, but you can probably figure all those things out if you spend some time actually playing with your cell phone and on the Internet.

Things become urgent when you decide that you are ready to date again. One-third of the 85 million baby boomers in North America are single, so it’s just a matter of meeting one.

What you may really need help on are the ins and outs of online dating, to which baby boomers are increasingly turning. 

Sign Me Up

While connecting online has become the norm, finding a likeminded friend or date can become frustrating—if you’re fishing in the wrong pond.

Take the time to visit sites before signing up.

If sites feel too juvenile, consider “mature” dating sites, such as Lavalife Prime, which is geared toward men and women who are 40-plus.

Alternatively, narrow the field by joining niche dating sites.

Places like, for bibliophiles, or, for music enthusiasts, or even, for single parents, connect individuals through specific tastes or lifestyles. 

All About Me

Now, the most difficult, most painstaking process: writing your profile.

Rather than agonizing over personal statements or — worse — selling yourself short, ask a friend to write it. He or she won’t shy away from playing up the positives.

But, says Jane Coloccia, author of Confessions of An Online Dating Addict: A True Account of Dating and Relating in the Internet Age, be honest. Don’t lie about your age, your shape, or your marital status (e.g., not yet divorced but separated). “The truth is always going to come out,” she says.

Picture Primer

As for your photo, think simplicity — and think current.

“If a guy is very attracted to a photo of you from 15 years ago and you show up older, grayer, and heavier, that is misleading and you won't charm them anyway with your personality,” Coloccia says.

“You are just setting yourself up for rejection.”

Coloccia advises to post a headshot (from the shoulders up) and a full body image.

“Men are very visual creatures. They are attracted to your looks first and then fall in love with the rest of the package” like brains, or sense of humor, she adds. 

It’s Your Move

It’s the dawn of a new era: No more waiting for the man to make the first move.

Guys love to be approached!

“The key is to create an immediate bond by mentioning how you have things in common,” Coloccia says.

“If he has a photo posted with a dog and you are a dog person, ask about his dog. If he mentions he loves to cook or has traveled somewhere that you have as well, mention that. Make the connection.” 

A final word of caution

Watch out for the “conquistadors,” as Coloccia calls them. 

“If a guy seems really into you right away, wants to meet immediately, and starts telling you how he is falling for you, and you haven't even met yet, RUN!” she says.

“Once they sleep with you, they are gone!” And whatever you do, don’t loan them any money.


Click the following to return to the directory for Sex and Dating Post Divorce

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1 comment

  • Comment Link Guest Saturday, 22 September 2012 18:17 posted by Guest

    Creating an honest profile: I have bipolar disorder type 2. Although I take medication and am stable, I feel that creating an online profile without telling someone that I have this disorder would be dishonest. If I were to leave it out, I'd be lying and if I put it in, I'm certain no one would respond. Besides that, I don't want people to know I have the disorder, so I wouldn't want to advertise it. I've been divorced since 2007, separated since 2005, and have not dated yet. I was with my ex for 20 years, so haven't dated anyone else since 1986. I'm 59 now. I also have been divorced a total of 3 times, which is bad. So every time I think about online dating I get stuck because I don't want to advertise my medical condition, I've been divorced 3 times and I pretty much feel like I'm damaged goods. Do you have any advice for me?