Stop And Think Before You Write!

Sure, online dating can be a numbers game, but nobody wants to be a virtual love-spammer. Ask yourself these four questions before emailing to another match to ensure you’re on the right track.

By Bob Strauss

wo hundred years ago, writing a letter to your distant beloved was a much bigger deal than it is today. You had to procure adequate supplies of fine parchment and ivory quills, squint at a hand-painted locket as you extolled your soul companion’s fine, plump lips and rosy, smallpox-free complexion, and not go all a-quiver as you affixed your wax seal to
Some people like the easy conversations that are possible on the Internet.
the exquisitely handwritten envelope. Nowadays, though, all you have to do is hunt and peck at the keyboard and hit “send” — one of the reasons so many cultured people still pine for the Age of Enlightenment (even if the average life expectancy back then was only 37 and girls got married at the same age most modern girls are trying to get their learners’ permits).

In fact, with most online dating services, it’s so easy to click the “email me” button while viewing even the most mildly intriguing profile that I feel I must provide a valuable public service to help you get the most out of that interaction. Here are four important questions you should ask yourself before you email any prospective sweeties, thereby saving both of you the fleeting awkwardness of pursuing a love that wasn’t meant to be. Are you ready? Answer them honestly!

Question 1: Am I really interested in pursuing a relationship?
Of course, this is a question you should ideally ask yourself before you sign up for an online dating service, not before you write to any given person. Explains Tonja Weimer, author of the books Thriving After Divorce, How to Attract Men and the online syndicated column, Savvy Dating, “some people like the ‘idea’ of dating and meeting someone, but can’t find the time to follow through — and some people like the easy conversations that are possible on the Internet, but prefer to avoid any real-life interpersonal interaction.” If you’re one of these types, that doesn’t make you a bad person — but it does mean you’ll be wasting the time of someone who’s genuinely interested in starting a relationship. (On the other hand, if you sense that the object of your desire feels the same way you do, go ahead and email, tweet, and IM each other to your heart’s content, secure in the knowledge that you’ll never have to actually meet.)

Question 2: Do I honestly see relationship potential in this person, or am I just trying to flatter myself?
Back when I was dating online myself, I’d often shoot letters to exceptionally good-looking women who shared the bare minimum of my interests — not because I seriously expected to strike up an enduring romance, but because I wanted to know that I somehow rated a reply. As ego-deflating as this strategy was when it didn’t work, it was even more self-destructive when it DID work — miraculously, I’d receive an upbeat letter back, allow my hopes to soar, send an even wittier reply, then never hear from her again (because, of course, by then she’d heard from even more eligible guys who actually knew
If you’re feeling burned out, turn your attention elsewhere.
how to speak multiple languages, or climb mountains… or whatever exceptionally good-looking women are looking for in a partner nowadays).

Question 3: Do I have something interesting to say?
Or, as psychotherapist David Sternberg phrases it, “Does my email sound like a form letter, or does it sound like I’ve put some thought into it? You shouldn’t make a bad impression before you’ve even had a chance to meet this person.” In my experience, if you’re writing an introductory letter to someone and you just can’t seem to muster up your usual wit, energy and attention to detail, that’s a sign that you’re not genuinely interested in the first place — or that you’re treating your online dating adventure too much like a real job (“I’m going to write to at least 10 people a day, whether I feel like it or not!”) If you’re feeling burned out, turn your attention elsewhere and try writing to the person a few days later — and if that still doesn’t feel right, deep-six that match and move on to the next likely candidate.

Question 4: Why am I writing this person and not someone else?
Weimer hits the nail on the head again: “Was it something negative that resonated with me, because I have a pattern of attracting and being attracted to ‘bad boys’ or ‘bad girls?’ Or were my heart strings plucked by the struggle, heartbreak, loneliness, abuse, or disappointment revealed in this person’s profile? If so, is this what I really want?” Ideally, of course, you wouldn’t have plunged into the world of online dating unless you’d already resolved these issues, either via psychotherapy, self-help books or frank conversations with friends. But before hitting “send,” listen to that still, small voice in the back of your head: it can tell you whether you’re making an honest attempt to start a lasting relationship or setting yourself up for yet another round of disappointment.

So, if you’ve asked and answered these four questions and feel ready to hit “send” anyway, forge on… and may the next reply you get be the one who wins your heart!

Bob Strauss is a freelance writer and children’s book author who lives in New York City. He’s also written the Dinosaur guide on, the online information network owned by the New York Times.
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