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Advice & More June 2015

With Wedding Season Here Again, Online Dating May Have New Appeal

By Teresa Ambord

Just like in regular dating, it takes time and trial runs to meet the right one. Don’t reveal your physical address too soon. Many people set up e-mail addresses and even phone numbers just for people they meet online, so that if it doesn’t work out, they can discontinue contact.

Dating was scary when we were young, and it’s still scary, but for different reasons. In some ways it’s easier now because we know what we want and we’re more confident. But the fact is, most of us 50 and up have baggage. The baggage might be a small duffle bag, or it might be a three-piece matched-set of luggage and a steamer trunk. It could be broken hearts, previous marriages, grown kids who don’t like the people you date, or worse, grown kids who still live at home, possibly with children of their own.

Online dating adds an element of anonymity, where we all try to be our best selves, and sometimes, try to be someone else. One man revealed through a dating site that he’d had previous unsuccessful marriages, which didn’t seem like too much of a problem to the woman he courted online, since she’d had two of her own. When they met in person he told her he’d had four failed marriages and a couple of failed live-in relationships. That was a deal breaker.

In addition to baggage, you probably have more assets to consider than you did when you were younger, and you want to protect them. Chances are you don’t have the career worries that you had in your 20s and 30s. And it’s pretty safe to say, you’re not concerned about birth control (unless you’re a man looking for a much younger woman). There’s a lot to consider, but, assuming you are brave enough to dive back into dating, how do you get started?


More Fish in the Sea than You Think

Don’t believe the naysayers that tell you your chances of meeting someone age appropriate are slim and none. In the 2010 U.S. Census, 78 million people were baby boomers and 30 percent of those people were single. That was five years ago, and the overall number of boomers is constantly growing. The number of people who are joining online dating sites – some that are specifically for the 50-plus gang – is soaring.


Is It Risky?

Of course! So is any form of dating. But as I said earlier, there is the anonymity to think about. You can create any persona you want to, and that means, so can they. The key is taking your time to find out the real person behind the online profile.

I have a friend who has been happily married to her online-catch for years now. They were originally from the same town, but had never met and then she’d moved away. They knew the same places, schools, restaurants. They spent months talking first through the dating site, then by e-mail, and then by phone. They fell in love, from a distance. Trouble is they both provided pictures of themselves that were flattering, but not recent. Okay, truth be told, who doesn’t want to post their best pictures?

Finally the day came when they met in person. They each took one look at the other and were both visibly disappointed, even annoyed. He had less hair and more belly than the pictures showed. Her face showed more lines and her figure, more pounds. Neither of them were superficial people, but they felt deceived. After a few uncomfortable moments, they were both ready to leave. Then, he said “let’s just take a walk on the beach before you go.” They walked. They talked. They remembered why they fell in love. Later I attended their wedding, where her Chihuahua – wearing a bow tie – was the best man.

The takeaways? This couple did much that was right, taking their time to really know each other’s hearts before meeting. But they almost blew it by posting old photos. We all want to look our best, but if you are going to post old photos, at least include the date they were taken. If you’re less than slim, post a full-length photo and the date it was taken.

Another woman I knew well was less fortunate. She rushed out of a bad second marriage and into online dating. Right away she met her “prince,” in a distant state. She was in love, she said. I ran into her in a store, where she told me she was picking him up at the airport that evening, for their first in-person meeting. She was buying a new negligee, which she sheepishly tried to tuck out of sight.

Soon after that first meeting, she sold everything, moved way, and married him. I lost touch with her, but heard she was extremely unhappy because once they were married, she realized he was bad-tempered and controlling.

The takeaways? Slow down. There’s a reason for the old saying, “marry in haste, repent at leisure.” Just like in regular dating, it takes time and trial runs to meet the right one. Don’t reveal your physical address too soon. Many people set up e-mail addresses and even phone numbers just for people they meet online, so that if it doesn’t work out, they can discontinue contact.

How can you meet safely? Relationship experts seem to agree on a few points:

  • Meet in a public place like a coffee shop, at least the first time, maybe a few times.
  • Meet during the day because it is less like a date and generally safer.
  • Drive yourself there so you can leave at will.
  • Say ahead of time, “I have an hour we can spend talking.” Obviously, that sets the expectation and lets you look at your watch and make a graceful exit when the hour is up if you want to.
  • Don’t leave the meeting place with him/her, especially to go “see his house,” or hers.
  • Tell someone you are going to meet this person and where.
  • Speaking for myself, I’d arrive early and park a little distance away from the meeting place. I’d want to see him arrive. Not that a fancy car is important, but at this stage in our lives, if he’s driving a jalopy that should indicate a problem.

Is it expensive? Some sites amount to $5 to $10 dollars a week. Like most membership programs, the longer you join for, the better the deal you get.

Online dating is what you make it. If you choose to try it, proceed with your eyes wide open and be honest. And if something doesn’t feel right, slow down.


Teresa Ambord is a former accountant and Enrolled Agent with the IRS. Now she writes full time from her home, mostly for business, and about family when the inspiration strikes.

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