WANTED: Flirting Critic

In the past few days I have lost three women I was flirting with. They all went dark. They are:

  • The 23 year old I mentioned yesterday.
  • Another divorcee that is possibly the full package. It is bizarre. We agreed to go on a trip to get away and she was all excited. HER IDEA. We agreed on available dates and to talk the next day to lock down specifics. “Poof!”–she disappears off the planet on me.
  • Lastly, the Midwestern woman whose Facebook conversation I am listing below.

I need to knock the rust of my game. I am guessing I blew it because my over enthusiastic response is a warning sign to women for whatever reason. Can someone confirm this? Is there any way to salvage the Midwesterner? I am exceptionally interested in going on a date with this woman because it allows me to peacock in front of some old nemeses. I would get the dual satisfaction being seen with her.

(Yes, I am a shallow SOB. At least in this particular case.)

Please critique the conversation below and offer coaching as necessary. I am thinking the Awesome at Online Dating Guru would tell me that I replied to her responses too quickly and then my last message was over-the-top with enthusiasm. I didn’t play it cool enough.  But I want that verified since I have been out of the game for 20 years. Would you grade it as an A, B, C, D, or F?

This is going to be more complicated than I expected. I am not a stalker, but I am an assertive and impatient person by nature. So this is going to be challenging I fear.


Yea, now that I proof read this post I definitely think I got carried away. To the point I am embarrassed to post this now. She gave me an inch and I took a mile. Wow. I really do need to work on my game. This is a major fail. I wish I had learned this lesson with someone else too. This is a costly lesson I fear.

I grade this an “F”. Or am I over-analyzing?

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10 thoughts on “WANTED: Flirting Critic

  1. I’m perplexed. When things genuinely click, one can never truly be overzealous, I think.

    Listen, is there any chance any of these women are reading your posts?! Being exposed in that way (even unnamed) might feel a bit creepy.

    Just wondering… and still rooting for you!

    • Thank you Elettra.

      I think the risks of these women discovering the post are minimal. It would be creepy. It should be creepy because private conversations should remain private. On the other hand, if I tried to summarize what happened I wouldn’t do it justice. So hopefully hiding the identities is decent compromise, and shows what actually happened so I can get good feedback, but does no harm to the writers. I hope anyway.

  2. Maybe a little too enthusiastic IMHO but it sounds like you’re a confident person by your conversation, and you certainly wouldn’t want to be overly reserved (definitely not a problem for you). Your blog is very interesting and look forward to reading more!

  3. I think you may have been a little too eager in your last response, but I don’t think all is necessarily lost either. For future reference, I probably would have said “yeah, maybe i’ll have to swing by [city] sometime,” and she how responds. If nothing else, chalk this up as a learning experience. Everybody gets shot down by somebody eventually; doing so will numb you to the experience. Once you lose that fear of being shot down, you’ll be more confident.

    BTW – Do these 3 know the status of your marriage? Is it possible that the fact you’re not technically “single” or “divorced” yet scare them off?

    • Thanks for peer review!

      Yes, I openly disclose my marriage purgatory to everyone and do not try to false advertise. The closer I get to breaking free the more responsive women have been, however, I am still not the ideal candidate for them obviously. I think the 23 year old is a typical 23 year old. I think the woman who bailed on the trip is flakey and crazy, so those two I am comfortable with. This Midwest girl I wish I had been smoother with. I will use OKC and try to find another woman in the area.

      The other thing I am reminding myself, is that women can go “all in” very fast. So they might have had dates with other guys that exceeded their expectations and they got swept away and forgot all about me. Which is nothing personal, someone else just beat me to the punch. Not hard to do with online dating.

  4. Ummm, compared to the communication I get from men on Match, this is WAY TAME. You seem fantastically normal. I get things from “Maybe I will love you” to “I can’t wait to have your mouth on my cock”. Before the first date, mind you. I think it is totally acceptable what you said, and I would be ecstatic if I were her to have someone so normal on the other end. Just wait til you get into online dating, it is INSANE. I’m done with it myself, as I will soon post about.

    • I made an OKC profile in the midwest last night and goofed around with it. What site are you using?

      I think you are making a mistake getting out. Taking a break is fine but don’t quit. Week after next I have some posts about it called the “Relationship Matrix”. (I know, I don’t know shit yet. But actually while in marriage purgatory I have observed friendgirls like I never have before.)

      You need to shovel hay if you want to find a needle in a haystack. Each bust is a step towards finding the right one. He is out there. You have to keep shoveling IMO.

  5. I think your game was fine until that final post. Yes, you prefaced it by saying that your coffee had just kicked in, but you had the right amount of learning about the woman and flirting with the woman, until you started to interrogate her. That’s a big turn-off, even in online dating, because 1) it does make you seem overeager and 2) it is soo much work for the person you are talking to! A list like that takes the fun and adventure out of dating and learning new things at new times.

    Now, I’m a fan of people being very upfront with me when it comes to flirting and, in general, I think that woman appreciate quick responses. No one wants to be kept waiting for a response when it comes to meeting someone you’re interested in. It can be confusing to know when you’re being asked out, and your “not-so-subtle hint” helped with that. I think my best advice is to just relax a little bit when you are in the initial stages of dating and conversation. Don’t take things too seriously, don’t jump too quickly. We’ve all done this at least once in our lives, but if you jump too fast you won’t know where you land until it’s in your house alone, wondering what went wrong, or after having run of with a crazy lady.

    Any other questions find me at my blog. I’m always around!

  6. Just a *little* over-eager, but don’t beat yourself up. My advice would be to move on completely from all three women; wait for them to contact you back. In the meantime, you can find NEW kindred spirits to connect with. Keep moving. Keep practicing.

    And whatever you do, *dont” get hung up on any one woman, for any reason. It’s decidedly unsexy.

    As you said yourself: you have been out of the game 20 years. You have to give yourself more time; have more patience! You are doing just fine given you are barely back in the pool.

    • Thank you for the words of wisdom and encouragement.

      Update: One of the women did contact me. Her Mom had a heart attack so I gave her a pass for going dark LOL…but not putting eggs in that basket, don’t worry. (Staying diversified.)

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