16 July 2013

Giving good text

By: Jessica B.

One of the hard parts about dating in your 30s is putting yourself out there. And dating in Chicago in your 30s isn’t easy. It requires a constant effort of going out, checking out profiles, looking at singles or matchmaking events (that don’t cost $500) and just…seeing what happens.

And while I’m not actively, obsessively looking, I’m open. And then a guy came around, who on paper was like, a yes. We were¬† the same age, had similar interests, we were looking for the same things, and he wasn’t damaged from past relationships.

First date went fine but where this guy really was a cut above was texting. He knew the right things to say when (I should note, they were genuine too), like “I should have kissed you on our first date” or “what would make me happy is a picture of your smiling face” or my favorite, “I get you’re busy, but I’ll wait for us to have dinner again, it’ll be worth it.”


Now, you could say, wow, you are starved for romance. And maybe you would be right, but really I think I’m just starved for a guy who knows what he wants, is confident in what he says (and means it) and isn’t going to put his dick in “one and done” women to figure out that free p*ssy is more fun. Cough, that happened.

So yeah, giving good text is hot. But that doesn’t mean it always lives up to in person. Sadly, this Robin Thicke of text went that way on date #2.

So what did I learn:

  • Gotta keep trying, this was encouraging but not the right one
  • Not so dead inside after all (yay!)
  • If I let you kiss me to “just get it over with,” that’s bad
  • Asking me multiple times throughout the date if we are going to kiss = not hot. At all

Back to the drawing board.


  1. Oh my. I went from being so excited to having the heebeejeebees!

  2. katelin says:

    he asked you multiple times if you were going to kiss??? oy.

    sorry he didn’t live up to his excellent swoon worthy texts.


  3. To KIss the Cook says:

    Oh buddy. We’re in similar boats. My hopeful ended over the weekend and I was needing that pep talk you just gave.

  4. Nora says:

    Giving good text is important! As is giving good face-to-face conversation; hopefully he will learn that for the next go round. And hopefully you find someone who has that quality, too.

    Love the “Robin Thicke of text” comment. That’s awesome. So are you :)

  5. HA! “Robin Thicke of Text,” that’s my new favorite line!!

    it’s so weird that I was having this conversation with my coworker yesterday. Only my problem is that I’m dealing with a boring texter. His texts are so boring and pointless that I don’t even want to go out with him, I keep putting off potential dates because I’m dreading how long or awkward the evening may be. Possibly this guy may give bad text but give good in-person conversation?

  6. Caryn says:

    all these experiences only benefit you in the long run. They help you fine tune and realize what it is you are and aren’t looking for. It helps you grow as a person and once you do find the right person to date, it will make you appreciate them even more.

    Sorry he didn’t live up to the texts.