a handy, dandy guide to dating in the digital age


Note: This post is a slight departure from the traditional high-minded chit-chat about mobile apps and technology startups…

Dating? Oy. Dating in the digital age? Yikes.

We live our lives online. We’ve adapted to publishing our every thought, concern, anecdote, humorous aside, EVERYTHING in public. Twitter, Facebook, Path…  you name it, we belong to it and if you’re like me, you tend to forget that there are people out there actively listening. Until that one time you happen to post something that could be slightly misconstrued and interpreted by a member of the opposite sex (or same sex if that is your jam) as “Hey! I’m single! Ask me out!”

…I apparently tweet out a variation of this every few months.

Anyway, this has happened to me several times: once a surprisingly happy experience that resulted in dating for a few months, once in an ambiguous “Did what I think happened just happen? No, thank you!” occurrence and most recently in an awkward please-make-it-stop spectacle.

“I’m glad I’m not a lady.” –dude who felt sorry for women as a result of these stories

Some gentle guidance seems to be necessary based on my experience, so I offer to you the Leslie Pro Tips for Dating in the Digital Age:

FIRST: Don’t ask someone out publicly. As in on your Twitter feed. (DM, while not ideal, is acceptable.) Don’t ever do this, no matter how long you’ve followed her and how fascinating you might think she is. It puts both of you in an uncomfortable position. You having a public trail of your inquiry. Her either ignoring you (not nice) or publicly saying no thank you (bitchy).

SECOND: Don’t tweet out to your followers requesting reasons why this woman (who, keep in mind, has not responded to your first solicitation) should accompany you to dinner. Just don’t. While nice, the inundation of kind words about you and why she should think you’re a catch are not necessary. In my case they only make me want to back away slowly. I mean, full disclosure: I like to be chased, but come on! It is too much.

THIRD: If your first few overtures have not been reciprocated, move on. Please? For everyone’s sake. Don’t @-reply her again over the following days with more reasons why she should go to dinner with you. This is when it starts to get creepy and you move firmly into 0% chance of date, 100% chance of being blocked land. No one wants that. We want to keep everyone’s dignity intact.

Lest we think I’m unfairly picking on anyone with this post, I surveyed my girlfriends to learn of their most disconcerting online experiences. Trust me, these types of things happen more than you’d think.

One friend has stopped posting to Twitter in real-time after a male acquaintance began appearing at her location as he “happened to be in the neighborhood.” Once or twice is a coincidence, but as it was happening so frequently it (rightly) freaked her out. As a result she’s checking in on Foursquare less and is tentative about social platforms in general where before she was an early-adopter.

Another girlfriend has a random person she went on one date with over two years ago consistently show up in her LinkedIn “Who’s Viewed Your Profile” section. Enough to make her wary and be grateful she’s not more active in other social media arenas.

In an attempt to tie this back to tech in some way, we’re stuck with these social mediums for now: Twitter, Highlight, Foursquare and the like. As has been mulled over before, if these companies want to survive women need to adopt them. If we’re barraged with unwanted advances, we won’t feel safe. If we don’t feel safe, we won’t use that technology. Refer to my post on Highlight for more thoughts on this. Something to keep in mind: “Just because you can [use these venues to ask a girl out], doesn’t mean that you should.”

Is this post harsh? Possibly. Will it result in a dating dry spell for me? Perhaps. It is a risk I’m willing to take because here’s the thing: how are men going to learn what works and what doesn’t if no one provides a little instruction? It is like that episode of Sex and the City that was so revolutionary for women. “Stop being weird online, you’re terrifying her!” is the new “He’s just not that into you.” I think it will totally work.

Oh, and I saved you the comments on how bitchy and pretentious this post is by tagging it appropriately. You’re welcome!