Fine Line Between Creepy and Cute in Dating

Communication is key in any kind of relationship. In dating, it’s vital.

I recently attended a conference at the Hyatt at Grand Central Station (NYC) and while walking there I decided to post my location on Facebook, just in case a friend happened to be in the area too. At some point (not sure exactly when) I had connected my Facebook profile to my Jcoach Twitter account (@jcoach1), so when I posted to Facebook I also automatically tweeted my location.

Not long after the Tweet I received a reply from the Hyatt concierge welcoming me to the hotel and letting me know that if I needed anything they were there to serve. Not only did I not find this to be creepy or intrusive, I actually was really impressed with their initiative and marketing prowess. Bravo Hyatt!

While this kind of proactive responsiveness is successful in the world of marketing, it could pose some challenges in the world of dating.

When it comes to social communication there’s a fine line between being viewed as cute or creepy. On the one hand putting in the effort to find someone’s contact info and get in touch with them to ask them out is admirable and might be viewed as impressive by the person you’re asking out. On the other hand, taking that effort a bit too far can put you right in the stalker category.

Ho do you know where the line is? There’s no clear cut answer…you need to apply common sense. The basic rule is that you want to respect a person’s privacy and not make them feel annoyed or threatened.

If you decide to cold call a dating prospect or arrange an “accidental” run it, keep it really light and super nice. Don’t be aggressive. You have no way of knowing what’s going on in the other person’s mind when faced with a stranger (you), so do everything you can to make them feel totally at ease. If it’s a face to face meet, make sure you do it in a very public place (not an empty subway stop at midnight). If you see that he or she is not being responsive to your advance, then back off and rethink your strategy.

One way to grab the attention of someone new without rousing any suspicions is via social media. Facebook and Twitter are great venues for initiating interactions in a subtle way. Let’s say you’ve got your eye on a woman you’d love to meet. You check out her profile (nothing creepy about that — it’s on Facebook) and look at the stuff she’s posted on her timeline. If it’s the type of post that’s open to intelligent comment — like an article related to a topic in the news — then go ahead and add your comment, as long as it’s on point and intelligent. Chances are she’ll read it and probably check out your profile. If she likes what she sees, she might engage in some form. If she does, great. If she doesn’t, then take a breather. Don’t start commenting on everything she posts. That’ll make you a stalker and even worse…a nudnick (as someone what that means). And being a nudnick is a huge turnoff.

Sending someone a friendly and well formed message is fine too, as long as it isn’t pushy.

There’s a whole mythology centering around the idea of continuous effort leads to positive results. Thanks, if you first do not succeed… That might be true for many things, but not necessarily when it comes to love. If someone isn’t interested in you now, the chances are that if you continue pressing them they’ll just strengthen their existing feelings and possibly turn them into disdain or fear. On the other hand if they are interested, there isn’t much you can do wrong, at least initially.

But if you aren’t sure how they feel, and most people aren’t, then the smart move is to use your common sense and stay out of their personal space — offline or on.

What do you think?

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