8 Secrets to Online Dating Success for Older Singles

I was newly single and back in Chicago. But I wasn’t the same single guy I was the last time I lived here. I was older and (hopefully) wiser. And I wanted to meet people, so I turned to Internet dating as a way to meet eligible women.

Over the course of several months of online dating, I discovered that the pool of available older women is vast and diverse (as is true of men, although perhaps to a lesser extent) and that with a little effort, a reasonably intelligent, halfway-presentable person can usually generate some interest on dating websites.

But things are different for older singles.

We’ve survived death and divorce, raised families, managed careers and built support networks of family and friends. And even though procreation is off the table, I picked up clear signals from the women I met online that the meter is running, so it’s best to get on with things. Most wanted to push past the introductory emails and calls to schedule a get-together ASAP. Some were intent on finding another lifemate in short order, while others seemed more interested in sampling different personalities and lifestyles.

Internet dating puts all options on the table, and a growing number of sites cater to the more mature singles crowd. My own encounters revolved around OK Cupid and Plenty of Fish, both of which are free dating sites. Here’s what I learned:

If you’re looking for someone of similar interests and lifestyle, the more specific you can be upfront, the better. For instance, does “loves sports” mean you’re up for cross-country skiing and white-water rafting, or is it a declaration that every weekend is devoted to channel-surfing the pro and college games?

Do you enjoy gardening or rebuilding classic cars? Do your politics dictate your worldview? What was the last good book your read, or film you saw? Potential dates skimming your profile are more likely to respond to specifics. Believe me, it’s a much better strategy than scheduling a coffee date and finding you have little or nothing in common.

If you’re not confident in your writing skills, reach out to a friend or family member for help. Just don’t turn your profile into Shakespearian-level prose that in no way reflects who you really are.

Here’s a surprise: Some women just look at the pictures! Men are often accused of focusing exclusively on the physical, but I soon realized there are plenty of women who do the same. This explains why several ladies in northern Wisconsin sent inquiries despite my stated intent to remain within metro Chicago for dating.

Since pictures are so important to your online profile, here are a few tips:

• Skip the bathroom selfies. Trust me, no one wants to see your personal care items or shower curtain. Move to another room (or go outside) and have someone else take your picture. A professional photo is a good idea, too — and if you do it right, you can wind up with one shot for your dating profile and one for your LinkedIn page.
• Don’t hide behind people or fashion accessories. If we can’t pick you out of your bowling team lineup or every picture features you in floppy hats and big sunglasses, you’re unlikely to draw much attention. The same goes for blurry pictures or too many photos of your pets, possessions or grandkids (no offense to the little darlings).
• Gentlemen: Keep your shirts on. Many women I spoke with were alternately amused and disgusted by bare-chested guys flashing their pecs in — you guessed it — bathroom selfies. Leave that approach to the twentysomethings.
• Ladies: The number of lewd messages you receive is directly proportionate to the amount of skin you display. I don’t mean those innocent bathing suit pictures from last summer; I’m talking about the negligée poses and excessive cleavage. A few women I spoke with were shocked — shocked! — at men’s easily predictable reactions to these photos.

Your profile needs at least one picture to get you in the game. You may be brilliant, handsome, wealthy and a great humanitarian, but you’re a non-starter without the visuals.

Are you looking for an occasional dinner companion, a friends-with-benefits arrangement or a marriage candidate? They’re all out there. The more clarity and candor you can muster (within the boundaries of good taste), the better.

A few dating sites allow men and women to fire off a canned “Hey, there!” message to interesting prospects. Better to write your own greeting and show you actually looked at the person’s profile. “I see that you love One Hundred Years of Solitude. That’s one of my favorite books, as well.” carries more weight and is more likely to get a response than a generic response.

Internet anonymity brings out the worst in some people, and there’s a certain amount of that in evidence on dating sites. “Fast Freddy ‘55” may think his bad-boy behavior is secretly a turn-on for women, but he’s deceiving himself. The majority of women I spoke with said they refuse to acknowledge crude come-ons.

Fortunately, most dating sites today are pretty well regulated, and the option usually exists to report inappropriate postings. And guys, before sending a message with even a hint of sexual innuendo, think about what your mother would say, then remember that many of these women are mothers, and even grandmothers, for that matter.

This applies to women in particular, but not exclusively.

According to the FBI, dating websites are often popular targets for scams perpetrated by offshore criminal networks. While the bureau acknowledges that virtually everyone is at risk, it says Internet scammers pay particular attention to “women over 40 who are divorced, widowed, and/or disabled.”

These cyber-criminals create elaborate profiles on singles sites, often with glamorous photos. Their goal: to separate you from your bank account. The FBI advises proceeding cautiously with anyone who:

• Professes instant feelings of love
• Claims to be a U.S. citizen but is presently traveling or working overseas
• Makes plans for a get-together but suddenly cancels due to a tragic event or
• Asks for money for a variety of reasons including emergencies related to health, travel or a financial setback

Bottom line: If the interested party sounds too good to be true, (s)he probably is.

A common gripe shared by many women I met concerned the fellow who arrived at the meetup bearing little resemblance to the guy in the profile. This advice applies to both sexes: Don’t post pictures of yourself from 10 years and/or 40 lbs. ago. Don’t rave about your intense exercise regimen when you’re really a couch potato. Don’t claim to be a gourmet cook when you can barely boil water. Don’t portray yourself as someone you’re not, because sooner or later your date will get a peek behind the curtain.

Take it from someone whose new “friend” ran up the bar tab while keeping her purse hidden all night: Start with coffee. Spend some time before you start spending money. The sad fact is that some people are just looking for an excuse to go out with anyone — especially a naïve chump who will pick up the bill.

Dollars aside, the first meetup should be brief. You’re just testing the waters. If the good vibes are mutual, you’ll be scheduling another get together soon, anyway. And if the date’s a bust, little is lost.

Many among us have a hardwired set of beliefs regarding how we appear to the outside world and what our ideal mate should look like, and we are disinclined to stray from our preconceived notions.

Case in point: After connecting online and hitting it off over an extended phone conversation, I met a woman for a happy-hour drink. She was an attractive redhead with a sparkling personality and a great smile. Things were unfolding beautifully, from similar interests to shared acquaintances. As our time together was coming to an end, I suggested a second date. Her response caught me completely off-guard: “You’re a really nice guy, but as a larger woman, I need a larger man.”

While “larger” is always open to interpretation, from my perspective, she in no way fit the general definition of the term. But that didn’t matter. She self-identified as such and envisioned herself with a man of more Falstaffian proportions, which I lack. Case closed.

Some of my cyberdates went nowhere, but a few women became trusted friends and confidants. I’m no longer active on dating sites, but I don't regret using them. For older singles in particular, these sites can be a great way to meet new people outside of your immediate social and business circles. Just let candor and common sense be your guide.

And skip the bathroom selfies. Seriously.