Basically you need to know when to hit reply and when to hit delete. When to trust the flirting and stick it out, and when to trust that it’s going nowhere. Do you really want to spend your 20th Anniversary at Hotmail instead of Hawaii? When your friends ask what he got you for your birthday, will you proudly exclaim, “250 MB of space on my email account!”

Trust me folks, when you get to the point of back and forth emails, 10 a day, every day, for a year, and don’t meet, there has to be a reason, and you better wonder what it is.

The initial contact via email is to either signal whether it’s a match, or to weed out the bad eggs. But when things click and you mesh, yet continue emailing and talk about meeting but don’t, then continue emailing… that’s a problem. But then the problem gets bigger. It escalates. Because the emails get better. And you think, this is ridiculous to keep emailing, but you don’t want to stop because you enjoy the emails, but you think if you enjoy the emails so much, you should meet. And you talk about it, but you don’t. So you email. And it’s a vicious cycle. And pretty soon, Mr. Hotmail calls you up and tells you he’s closing your account if you don’t delete some of Flirty Phil’s emails. Because of course you’ve kept them all in your inbox because they’re so damn cute.

I am a happy little emailer, but does that mean if I meet someone via email, I only want to correspond with him that way? Isn’t the point of “meeting” someone to “meet” him? Shouldn’t meeting via e-mail lead to an actual meet with human interaction? Or can you be just as happy “knowing” someone over email?

I was in a like situation, receiving emails from someone, not having met in person, but associated with him via work channels. It was months of frequent emails, but I was perfectly content with the email situation. On the outside, I’m sure it looked bizarre. But really, I was just excited to click open my inbox and have a new email. Oh come on, you know what I’m talking about. In the back of my mind, I knew it was a little strange to not have met but to have such frequent email miles. It got a little confusing after a while. If I read something one way, it could be sarcastic. Another, flirty. It was all a little exhausting to keep up with and interpret, but I did. Because it was nice to have an email to turn to every day. But is that what we want? An email to turn to? Shouldn’t it be an actual person? I will tell you this. After many, many months, we did finally meet. We’re back to email. So maybe it is just an email thing, and we can leave it at that. But at least I know. Sort of? I’m not gonna lie, I still like the emails. But I’ve learned that maybe it’s something I shouldn’t get too wrapped up in. Being strictly textual just doesn’t work and can be a bit confusing when establishing what your relationship actually is.

For all of you other daters who feel like you’re in a episode of the Twilight Zone, trapped inside of your email, here are some tips. Whether you hit reply or delete is up to you. Maybe he does want to meet and is just a little shy. Do you two click and does he seem to want to pursue a relationship? He may be a bit of a coward, and that’s okay. Take the reigns. Hit reply, and demand a date--in a sweet, non-threatening way, of course. It can be awkward meeting someone you’ve only “met” via email, so do your best to make it not awkward. But maybe he doesn’t want to date. Maybe he likes his email, and you know what? Maybe he just wants a pen pal. Yep, a pen pal. If you’re okay with that, great. We can all use more friends. And who doesn’t like a nice email to read? But if not and you feel a little misled, and that is definitely a strong possibility, then it’s a simple move. Delete.

There should be a cutoff point. It’s what the experts say. After a few emails, if you don’t meet, you should give up. Because you’re falling for the email address, not the person behind it. It’s easy to read an email and believe something is there that isn’t. I always ignored that because I didn’t want to believe it, or because I figured that it wasn’t happening to me. The truth was, I liked my emails. It was nice to have someone to correspond with, no matter where it was going. But maybe it’s not knowing when to hit reply or delete. Maybe it’s just knowing when to sign off.