How To Write Online Dating Emails That Get You To The Next Step


How To Write Online Dating Emails That Get You To The Next Step
There's an art to writing online dating emails that will get him to call you. Here's how!

Online dating emails can be tricky. You have a small window to make — or break — a first impression. You can't hear his voice, so you don't know the true intention behind his words. Be particularly careful about what you write and how you react to what he writes. I recently had a fun email exchange with a man on OKCupid. I'm sharing it as an example of how to write online dating emails that will get him to call you (I changed his name to protect his identity). My notes are in parentheses. Several times during the exchange, I could have stopped the conversation cold with the wrong response. I thought I handled it with humor and a light heart. What do you think?



I had thought to arouse your attention with wit, humor, and good 'ol down home ludic narratology or maybe my famous Fish and Grits, so says my daughter. But, I get ahead of myself, and resolve to something simple, sweet, and not too forward. Let me just say that our OkC stats look promising. Would you like to meet for tea or a drink (I'm thinking Sangria), and explore what's behind the numbers? Maybe we can figure out OkC's "Match" stats. From your profile, I submit OkC needs a new algorithm. – John




You had me at 'ol down home ludic narratology. What's a man with a smart mouth and smart hands {I used humor and referenced something in his profile about his smart hands} doing on a site like this? Searching for a warm, whacky, whimsical woman like me, of course. Margarita or Sangria – sounds like you'd make a fun drinking companion. Just be warned…I’m a lightweight. I can get tipsy off a half a margarita. {I wanted to let him know my drinking habits upfront}. Just enough to discuss the wisdom of OKCupid’s algorithms. So, why would my profile inspire a new algorithm? {I ended with a question. It's a good idea to end your emails with a question if you want an answer!}

Looking forward to learning more about you, {I let him know that I want to hear back. Give a man encouragement. He'll respond well to not having to guess how you feel.}

Sandy {I share my first name with a man who has potential. Some women like to share an initial or a nickname until they're comfortable.}



Hi Sandy, 

Warm, whacky, and whimsical of course, and a cheap date. Ha. Truth be told, I’m a one glass kind-0-guy my self. {I like that he revealed his drinking habits. That was sparked by my comment about the 1/2 Margarita.}

Do you get into the city much? {As a resident of Connecticut, which is less than an hour from Manhattan, I get this line a lot. My first reaction is, Is he really that lazy? Won’t leave the city? I’m a woman of value. He should come to me!} I’m on the Upper West Side and work in Midtown. - John


Hi John,

Hey, I never said I was a cheap date. 1/2 a drink maybe, but there's nothing cheap about me, baby. {I could have been offended about his comment that I'm a cheap date. I chose to be playful instead. Choose lighthearted over angry and reactive. You'll be glad you did.} Glad to hear you're a one drink kinda guy. I like that. {I let him know that I value that he's not a heavy drinker. Good to discuss values in these subtle ways even before a first date.}

I do come into the city for the right kinda one-drink guy. But I'd like to know more before I make the trek in. Let me know if you're up for a chat to see if there's enough intrigue to land the 1/2 drinkin' chick from CT. - Sandy {Again, I used humor to diffuse how I felt about him asking me to come to the city. And I stated my self-worth by saying that I want to talk first before making the trip in. Let’s see if he's worth the trip…but I wasn't bitchy at all about it.}

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Article contributed by
Advanced Member

Sandy Weiner

Dating Coach

Sandy Weiner

For a copy of my FREE report, “The Top Three Mistakes Midlife Daters Make (and how to turn them around to find love now)” please click here.

If you are serious about finding love this year, there’s nothing like group coaching to keep you accountable and give you solid dating tools that work. In the Last First Date Inner Circle, you'll have access to two monthly topic-based Q & A calls about dating over 40, and a private forum for you to connect and share your experiences. All calls are recorded and transcribed, and you get a free chapter a month of my upcoming book. If you're a woman over 40 and want ongoing coaching support at an affordable rate, check out the LFD Inner Circle today. 

Location: Stamford, CT
Credentials: ACC, CPCC
Specialties: Dating/Being Single Support, Empowering Women, Online Dating
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