The Over 50 Step-by-Step Guide to Online Dating

Last month, I wrote a piece on the differences between what men worried about when they were dating in their teens (“Will she laugh at my peach fuzz?”) compared to their concerns when dating Over 50 (“Will she laugh at my back hair?”). You can read the other 24 here.

When it comes to overall changes in the world of dating between then and now, the very best improvement has to be online dating. Truly, it’s an historic innovation that ranks up there with the cotton gin, penicillin, and those lights in the parking garages that show you which spaces are empty.

Online dating just makes everything so simple.

Instead of spotting someone of interest; figuring a way to get to know him or her; doing your best to make a good impression; then working up the courage to ask her out (man) or hoping he will (woman), you merely fill out an online form, add some pictures, click a button, and boom: it’s game on.

How that game will go is impossible to say. Maybe you’ll find the love of your life, as the various online dating companies all seem to promise. Maybe you’ll engage in a steady stream of short-term, non-committed, sexually-driven encounters as a few of my friends did. Or maybe, like me, you’ll just have a nice time and meet some interesting people (okay, fine, I know what you’re thinking — yes, of course I’m envious of those friends…).

If you’re single and considering a full profile site like Match or OKCupid, or if you’re in a less than ideal marriage and wondering about online dating (check out this article on that situation), here’s a step-by-step look at getting the process started:

Get a separate, nondescript email address. You can do this for free through gmail, hotmail, yahoo, or others. Privacy is certainly a factor, but it’s also easier to keep your dating correspondence separate from your regular personal and business email. You’ll get lots of emails from your dating site, and hopefully a flood from people eager to meet you.

Choose your dating site screen name. Dating site screen names span the entire gamut. People use first names or initials, a personality trait (Loves2Laugh), a favorite activity (GolfNut), their hometown (LABabe), their profession (ElMatador), or a combination (NYCDocRuns). It’s wide open, and gives you a chance to highlight something(s) about yourself to catch their eye. So be prepared before you go online, recognizing you’ll likely have to add random characters (zip code, birth year, underscores) to achieve uniqueness. If you use a full-sentence-in-a-screen-name like “Imaybthe14U2luv4evr,” chances are good U will B 4gotN.

Add pictures. Okay, here’s a fact: your primary picture will make or break your online dating experience. But wait, you say. I’m on a full profile site because I abhor the shallowness of swipe apps like Tinder. I’m so much more than my picture; I’ve got hopes and dreams and wit and style, all of which I need to express fully so potential dates will know the true me, inside and out.

Yeah, that’s great. But if they don’t like your picture, they’re not reading a word you wrote.

Which isn’t to say you’ve got to look like a movie star to succeed at online dating. Of course not. But you’ll have much more success if you look your best. A clear shot, a nice smile, and bright eyes will help you score points. (An Over 50 photo tip: looking up at the camera can help prevent that mess below our jaws…) Avoid hats, sunglasses, and being too “artsy.” And this shot must be mostly your face — if you’re turned away, or you’re too small to really make out, you’re going to get passed on.

Then add at least four or five additional pictures. They should both prove your primary shot isn’t a fluke, and illustrate other aspects of your life. You might include photos with your kids, your dog, traveling, hiking or biking, perhaps a business portrait. At least one should show your body head to toe. And make sure you’re consistent. You don’t want someone to click through your pictures and go, “Wow… very nice… excellent… oooh, that’s too bad. Pass.”

Your pictures must be fairly recent. Not yesterday, but not last century. It makes absolutely no sense to post old pictures, then show up looking like the parent of the person your date expected. At that point, there is zero chance you’ll win him or her over with your sparkling personality. And if you do have to use a great shot from the 00’s, cop to it and put the date in the photo’s caption.

Remember: a photo transmits a tremendous amount of information. Be aware of that fact when choosing yours, and when browsing other’s.

Write your profile. Different sites will have different formats, but a few basic concepts apply.

First, be brief. Shakespeare didn’t know from online dating, but his “…brevity is the soul of wit” is spot on. Nobody is going to wade through through a fifty line block of solid text about what you’re looking for in a soul-mate. Thanks to the internet, most people just skim, looking for nuggets of interest. Make it easy for your reader.

And secondly, stay positive, but be honest and show some humility. Nobody’s life is perfect, and portraying yours that way won’t make you look good. You’re over fifty and single — something didn’t work out at some point along the way. And that’s okay, since it’s the same for the people reading your words. By all means emphasize the good things in your life, but noting you’ve had a down or two among the ups only makes you more genuine, relatable, and approachable.

Answer the questions. Here you’ll have a chance to choose pre-selected answers about yourself, and what you’re looking for in a potential date. First biggie is age, and again the suggestion is to be honest. Some people list themselves as younger for “search purposes,” then tell the truth in their profile; that’s not as bad as using ancient pictures, but again gets you off to a bad start. Similarly, be honest, or at least honest-ish, for questions about your height, body-type, exercise frequency, etc.

As for questions about what you’re seeking in a date, go as broad as possible. List yourself as open to a wide age-range, at least a bit beyond your own. For topics like religion, ethnicity, hair color, etc., select “no preference” as often as you possibly can. Showing how open you are makes you look better to people inspecting your profile, and should lead to more contacts. You’re under no obligation, so why not have as many options as possible (and really, are you so “toned and athletic” that you’ll only date someone who’s likewise)?

Go Live. Launch your completed profile on a Sunday. Then get busy looking for people to approach, enjoy the contacts that pour in for you, or both. If things go well, you may have dates set for the very next weekend, and be off and running.

Next week we’ll look at approaching people you’re interested in, evaluating and responding when you’re contacted, setting up that first date, and the date itself.