The Over 50 Step-by-Step Guide to Online Dating, Part II

Recently I posted an article that offered Over 50’s a step-by-step guide for getting started on a full-profile online dating site. It included tips on choosing a screen name, adding pictures, and completing both the “essay” and “multiple choice” portions of their profile. It’s available here.

Now, let’s continue with the next steps after your profile has gone live.

Approaching people of interest. If you’re a man who wasn’t the smoothest operator in your twenties, or a woman who felt constrained by the dating etiquette back then, this is where online dating really shines. For both men and women, it couldn’t be easier — just spot someone who looks good, check out their details, and if you’re interested, hit them up.

Whether your dating site suggests candidates or you initiate a search, you’ll find yourself staring at the photos of dozens of potential dates. As I said last time, the primary photo makes or breaks the online dating experience. And you’re about to prove me right by clicking on the photos of people you find attractive, and ignoring the ones you don’t.

Clicking on someone brings access to more photos, as well as his or her written profile. Take in the pictures, and read (or at least skim) the words, but at this point just browse a bunch of profiles, getting a sense of who’s out there and how they present themselves. You’ll begin to see stand-outs soon enough.

One note about browsing: On many sites, the person you looked at will know you paid them a visit. Not a big deal if you do it a couple times, but continually checking someone’s profile may seem a tad “stalker-like” if you do contact him or her later.

Once you’ve identified some ladies or gentlemen of interest, it’s time to reach out and contact them. Different sites may allow users to send a “wink” or a “smile.” Or they let you “like” or “favorite” someone, informing your target after you’ve done so. Not a fan of this approach, nor sending a single word greetings like “Hi,” “Hey,” or “Yo.”

Instead, man- or woman-up and send your target a real message. It couldn’t be easier, and you’ve got nothing to lose. An effective approach is to say you enjoyed his or her pictures and profile, noting an aspect or two that stood out. Then suggest he or she check out your profile, and if there’s a reciprocal interest, you hope to be in touch. Sign your email with your real first name, which adds a more personal touch, and click SEND.

So you’re done, right? Just sit back and wait for a response?

Nope. Do the same thing again, for someone else you found interesting. And again. And again.

It’s a numbers game, like a client-based business. You’ve got to put as many people as reasonably possible into the funnel, because you’ll lose some at each step along the way. The more candidates you feed in, the more opportunities you’ll have to actually connect.

At the same time you’re contacting your targets, others should be contacting you.

Evaluating contacts and responding. It’s not clear whether writer James Thurber or baseball broadcaster Red Barber coined the phrase “in the catbird seat,” but clearly that’s where you’re sitting, as messages from interested online daters fill your inbox.

The messages you receive will run the gamut, from those pointless one word exclamations, to full autobiographies. You’ll probably open all of them, but again the photo will inform the enthusiasm of your click.

If you do like what you see and read, and are interested in moving forward, answer back with a short note. Express appreciation for the contact, cite something you liked from his or her pictures/profile, suggest a phone call, sign with your real first name and, if you’re comfortable, cell phone number.

If you’re not interested, it’s okay to just ignore the approach. Though you’d never do that in real life (right?), it’s kosher online. Just remember, it works both ways: if you ignore some of the people who contacted you, you can’t get upset when you don’t hear back from some of those you approach.

Setting up the first date. One important note: no matter who made the first move, don’t let the process drag on. The longer it takes to get together, the less chance you actually will. If you get a “Let me check my schedule and text you next week,” don’t hold your breath.

Once a mutual interest is established, try to set up a phone conversation.

For many of us, this phone call will be awkward. But remember, you’ve got a great cheat sheet: his or her profile. Do some preparation by re-reading it, and perhaps even have it open on your computer while you talk. That information should help you make conversation, but don’t burn it all up on the phone — save some for that first date you hope to have.

The goal here is to see if there’s any sort of connection between you two. Just as you gain a lot of information from a person’s photo, you’ll similarly get a good read through a conversation. Is he or she energetic, interesting, funny, charming, smart?

If you like what you hear, slide the conversation to getting together. As you’ll know the other person’s basic location from his or her profile, be prepared to suggest some meeting spots. Most people prefer doing coffee or a drink initially since a full meal seems like too much of a commitment.

If, however, you’re not interested, you can always say “It was nice speaking with you, but I just don’t think it makes sense to get together.” It may seem hurtful, but you’re really doing yourself and the other party a favor — if it’s not happening on the phone, why put in the time and effort of meeting up?

The First Date. It’s always a good idea to be early, as you can get settled and keep an eye out for your date. You’re probably pretty familiar with his or her appearance, but it couldn’t hurt to have your date’s picture up on your dating site’s phone app for a quick check.

Once you’ve spotted each other, there’s the awkward “handshake or hug” moment. As the man, I felt that was the woman’s call, and waited for her to indicate what we were doing. And speaking of the man’s role, I also considered it my responsibility to pay on the first date. Apparently, my dates overwhelmingly agreed, as only a couple ever offered to split the bill.

But the key is, you get a chance to sit down with the person you first knew digitally, and then via voice, to see what happens when you’re actually face to face, breathing the same (coffee or alcohol scented) air.

Not trying to tell mature adults how to conduct themselves on a date, but here are a few reminders that should help you make a better impression:

Do more listening and less talking. Ask good questions, and pay attention to the answers.

Whether you’re divorced, widowed, or have never been married, the question of why you’re single will probably come up. Have at least a notion of how you’ll answer it, and be sure that answer is free from anger or bitterness.

Remember, it’s just coffee or a drink. If you can go in with a relaxed approach and no expectations, you’ll be putting your best self forward.

You’ve heard it all your life, and it’s still true: Be yourself. Showing your date who you honestly are is the best way to get the same back from him or her.

And then, if it works out, and there’s a real connection, and you’ll be seeing each other again, congratulations!

And if that’s not the case, you deserve congratulations, too. You’ve met someone new, you’ve had an experience that helps you grow, and you’re one step closer to finding that right person who is out there waiting to find you, too.