Successful Online Dating Part 6: Being engaging

Okay, so you have a compelling profile, some snazzy pictures, and now it’s time to complete the action:

Get out there and make conversation!

There are two ways this happens, and you have to be prepared for both.  The first is that someone happens upon your profile either through their filtered search or through a site suggestion, and they contact you.  The second is that you find someone interesting and you message them.

First contact protocols

Here is how to not get a lot of responses:

“hi babee ur hawt wanna fuk”

“how are you today?”

“wuts yer favrit sex posishun”


There are multiple problems with these.  First, there’s next to no spellchecking or grammar going on.  Second, there’s nothing attractive or appealing about them.  Third… do I really need to explain more?

Making contact with someone is about initiating a conversation, starting a process of exchange, not about negotiating the price of immediate sexual intercourse.  (Of course, there are some places like that, but we’re talking about dating here, not just hooking up for the night anonymously.)  If someone took the time to write a profile, take the time to read it.  There will be at least a few cues in there about their interests, and if they resonate with you, mention it.  Here are some of the real phrases I’ve used to initiate contact with someone:

“You like BSG, Firefly, and you’ve seen ‘the Man from Earth’?  I bet we could talk for hours.  What did you think about John Oldman in MFE?  Was he making it up, or was he telling the truth?”

“I just had to drop a line and say, I *love* your hat!  You look so dapper in it!  Where were you when that photo was taken?  Is that White Rock Lake?”

“I’ve always thought it was rude to add someone to Favorites and rate them highly without contacting them, so I’m dropping you a note.  I know we’re a couple of states away from each other, but we have so much in common.  It’s not everyday that you run into someone else who has read the entire works of Hakim Bey.”


See?  And everyone one of those messages started a conversation that went a pretty far distance.  I’ve even been out with two of them.

Before I hear the whining and complaining from the menfolk about how it’s so easy for girls to get responses from guys, pay close attention:  It’s not about getting a response, it’s about establishing a conversation, which is an integral part of recognizing another human as a human.  Ideally, it’s a human that you’re trying to find a relationship with.

How long does your first contact message need to be?  You should probably keep it around a decent paragraph – five sentences or so – with questions and statements both.  Perfectly delightful people have been passed over either because their first contact was a single sentence of no substance or because their first contact was a veritable wall of text that responded to every single statement made in a profile.  In both cases, the intimidation factor is immense because there’s nothing for the responder to work with.

When and how to respond

You’ve received a first-contact from someone, and now the onus is on you to decide how to reply.  I realize that I’m a strange duck because I literally reply to every single message I receive.  That’s not to say I start a full-fledged conversation, but I do reply.

Here’s what happens:  Guy Smiley contacts me, and before I respond, I check out his profile.  Do we have a lot in common?  Is he within my age range?  Is there any kind of underlying manipulative or passive-aggressive language in his essays?  What does he look like?  Would I be crushed under his weight or would we clatter together like a couple of bags of bones?  Does his overall style appeal to me?

If he’s appealing and he’s given me an in (a question or leading statement that is more than a generic compliment), I answer his question with an answer and try to make my response around twice as long as his for very short messages and about the same length as his for longer messages.  The same is true for the opposite gender, and I’ve found that most people naturally respond in about that length to my first contacts as well.

If he’s not appealing to me, I will try to write a polite yet specific statement about why I don’t want to pursue a conversation.  I have said all of the following:

  • “I’m sorry, I’m old enough to be your mother.  That may not be a problem for you, but it totally ooks me out beyond reason.”
  • “I’m deeply flattered by your advances and I’m sure your cock is significant, but I’m not really interested in that kind of liaison.”
  • “I looked through your profile and it seems that we have absolutely nothing in common.  In fact, we’re gauged at over 60% enemies besides the 8% match, and I’ve found that this number pretty accurately reflects what kind of spontaneous conflagration would happen if we occupied the same space for more than five minutes – and I don’t mean that in the good, happy, fun way.”
  • “I’m not really sure what language you were using in your message to me, and Google Translate couldn’t figure it out for me.  I’m afraid I’m not quite skilled enough at charades to try a relationship with someone despite a clear language barrier.”
  • “Oh, gods, no.  I have no idea what on earth you’ve learned about speaking to other humans, let alone females, and not even getting into the question of the anatomical possibility of such a thing, but your continued singleness is not a mystery.”

And for every one of them – including the last one – I ended the response with “But good luck on your search.”

Every now and again, someone will write back after I’ve sent a considered rejection and thank me for my time, and often they will ask what I felt they could do better.  I try to help where I can, and sometimes it turns into a pretty reasonable friendship – a guarantee that it will go nowhere romantic or even in-person, but at least we can laugh about some funny faux pas we run into.

A final thought

Regardless of the kind of relationship you’re looking for, being polite and respectful will get you a lot further than vulgar and tacky.  Being nice to someone doesn’t cost you anything, and if you’re afraid that even responding a little will cause a problem, there are things like “block” buttons and “report user” links.  We’ll talk more about how to use those later.


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