Can somebody fill me in?

I’ve recently been noticing a trend that’s probably existed all along but that I didn’t realize until now—I have no online dating game.

Don’t get me wrong. I know that in person, I have the capacity to be friendly, outgoing and at least mildly interesting. But when it comes to the “behind the screen” communications, I think I’m falling short. Last week, I was chatting with someone. The convo was going well, he seemed interested. At a natural point in the conversation he asked if I’d like to get drinks sometime. I looked at my calendar and realized that my next free night, other than that evening, was the following Monday. It was a Tuesday.

As we all well know, momentum is everything with these things and a week in between a proposal of a date and the date itself is a pretty awkward amount of time. Do you keep chatting? Chat sporadically? And if you do text this whole time, aren’t you kind of eliminating all the small talk that first dates are predicated on? Either way, I figured a week was not really an option so, I responded, “I’m free tonight or next Monday.”

I’d recently purchased that silly feature where you can see read receipts on this particular app and, after noticing he’d read the text—and not responded—whereas our communications up to that point had been pretty steady, my heart fell. What did I do wrong? He asked me out and then disappeared.

I went to the best focus group around—my other single friends—and asked for their advice.

  • Oooh…you came on too strong
  • Hmm you seemed too available proposing that evening.
  • You should have let him propose the date

On top of just feeling bad that I’d clearly missed out on my chance with this guy who was employed, handsome and seemed relatively normal (a rarity these days), I sat back and said “what the hell.”

Who made these rules? When did we decide that responding to a person asking you out with some days and times that worked for you was “coming on too strong?!:

You’d think that considering how long I’ve been doing this, I’d have figured it all out but I still have very little clue as to what the rules actually are. I try to always be myself which means responding when I see a text come through (rather than waiting for hours or even days), being direct and honest, and generally trying to avoid any game playing. But apparently, to succeed in this crazy world, these are not the rules to live by. So, since everyone seems to have gotten the rulebook except for me, here are some outstanding questions I have:

1. How long is an appropriate time to wait before responding to a text?

2. How long after a date are you supposed to wait before getting in touch?

3. What’s the fine balance between playing hard to get and showing you’re interested?

4. Are you supposed to let a guy walk you home after a date even if you don’t want him to come up?

5. What exactly qualifies as over sharing?

Just for the record, I’m asking these questions rhetorically. I don’t think there are any hard and fast answers and the hopeless romantic in me still hopes that if it’s the ‘right person’ it won’t matter what you do or don’t do. But hey, if you have any amazing rules that you live by, I’d love to hear them.

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