Let’s Analyze this OKCupid Email Exchange, Shall We?

Posted by in communication skills in dating, dating in midlife, online dating after 40 | 0 comments

OKCupid email exchangeThere are all types of people dating online. The good, the bad, and the crazies. I encountered one of the crazies recently, but it wasn’t immediately obvious that he was immature, overly sexualized, and a lazy bum until we began emailing. According to OKCupid, this guy was 84% match/11% enemy. That’s based on their algorithms for matching people online. When he showed up in my weekly matches, I checked his profile. He was handsome, and I liked some of what I read in his profile, but not enough to send an initial email. However, he saw that I opened his profile, and about a minute later, I got this email…

Him: Thanks for taking a peek. The geniuses at OkCupid say we match!
We agree?
Me: Yes, they are geniuses at matching aren’t they? I’m willing to prove them right. How about you?
Him: Ready, willing and able!
When are you in NYC next?
Me: Not sure. Injured my clutch pedal driving left foot 🙁 and can’t go very far. When are you in Stamford next, Mr. Ready willing and able?
Him: Ha ! not sure when I am in Stamford CT next….
that is a long trip, an “overnight” trip, if you catch my drift.
I am a Manhattan creature, never owned a car.
I will make the trip by train, if it is more than just a coffee date… sounds tempting?
Me: Let me get this straight…you’d be willing to take a 45-minute train ride if I sleep with you?


Me: If we were in a relationship – sure. First time meeting? You’ve got the wrong woman.

Him: Got it. no problem. we can meet in the city for coffee if you happen to be in town.

Me: (no response)

Him: Do you usually date younger men?

Let’s analyze this OKCupid email exchange, shall we?

Started out innocently enough with him noticing that I checked him out. While I wouldn’t recommend using this direct approach to a client, I do strongly recommend that you check out the men who check you out. On Match.com, you click on “Who’s Viewed Me” under the Search tab. But don’t say, “I saw that you checked me out” or “Thanks for taking a peek”. Just email the guy as if you stumbled upon his profile on your own search. You’ll come across as less stalk-ish, more confident.

Notice that I was flirty and used humor about the matching algorithms. I was also positive in my approach, writing, “I’m willing to prove them right”. Takeaway: stay positive, open, flirty, and fun in your email exchanges. Rule a man in instead of out – until you have reason to rule him out, as I did in just a sec…

“When are you in NYC next?” This statement triggers a negative response in me. What it says is, “I’m in NY and if you want to meet me, you’ll need to make the trek. I’m not putting in the effort to come to you.” Dating outside of your immediate geographic area can be challenging, but you don’t need to react negatively if men want you to travel to meet them. You can suggest meeting them halfway, or do what I did…

“When are you in Stamford next, Mr. Ready, Willing and able?” Notice that I didn’t lash out at him for asking me to come to him. I was playful, emphasizing the words he used – ready, willing and able. If he is indeed all of those things, he’ll want to make the trip for me this time, won’t he? Let’s see how he responded…

He tells me that the trip is too long for just coffee. He wants to do an overnight, to sleep with me on a first date. Nothing like getting right to the point, huh?

By now, this guy is history, and I am direct with him. “Let me get this straight…you’d be willing to take a 45-minute train ride if I sleep with you?”

His response? “OF COURSE!” Don’t you love the all caps?

He’s officially in the “jerk” category. Notice how he responds when I essentially tell him,  “no way in hell, buddy”. He’s back to, “we can meet in the city if you happen to be in town.”

That doesn’t deserve a response. And neither does the follow-up statement, “Do you usually date younger men?” He’s four years younger than I, and yes, I date younger and older men. I don’t look as closely at age as I do at character. And this guy could use a boost of manners, character, and chivalry.

Did you find this article helpful? Please let me know, and if so I’ll continue to share real-life email/text exchanges so you can learn what to do and what not do in online dating.


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