Do I Need a Timeout?

So since the end of Ed I have gone on dates with a couple of guys. I’m trying to be more intentional with the guys I’m engaging and going on dates with. This along with my charming personality should make for a love match…. right? … right?

HOWEVER, there is a joke that Sean used to say to me “Jill, for writing about dating and having a podcast you are seriously horrible at it.”

This joke was in relation to all the stupid things I said on our first date. (Stories about Exes, “sleeping” habits, and I think the words ball gag was used at some point.

Luckily for Sean and I, we had met at a bar and had a normal relaxed conversation before I was in the context of a first date. In the beginning I thought he was gay so there was ZERO pressure and I was just me. This was lucky for him… the recent dates I’ve been on haven’t been as lucky.

I went on a date recently that if it had been recorded… could be put on VHS, played on a TV cart and brought into a room with young single adults as a “What Not to Do” after bar special.

In this date you’d be able to see the below choices:

cue cheesy 90s music and graphics here

  • Anything your date says he enjoys make sure to hone in on any detail that would stress how that much you’re not like him – don’t spend a second talking about how you’re similar
  • When your date tells any story relate it directly to a dating story that you had with an ex – *Bonus points* – if you can bring up 2 exes in a story
  • Make sure that you never show your soft side and even call yourself an alpha female
  • Try to curse as much as possible (even when they do not) and if you can make a Jack off hand gesture multiple times with an eye roll know you’re winning

Yep… all of these things happened…in one date. The worst part was I thought the date went WELL and kept thinking “man this dude is checking all the boxes” and pretty promising.

I even almost messaged him at the end of the night to say I had a great time. Luckily he texted me first saying he didn’t feel a connection. Yes I was disappointed at first. Then I started replaying my date and I was just embarrassed.

This seems to be a common theme in my recent dating life. Read my previous blogs and you’ll see it. While I am trying to be more intentional about who I am dating I also need to be a lot more aware of who I am when I’m dating.

In my next date, you’d be able to see the positive side of the lessons: (I WILL make this happen!)

  • Anything your date says he enjoys make sure to ask additional questions and try to find common interests
  • When your date tells any story, listen and then if you have a funny story (with your friends or family) add to the story – no need to ever mention an ex
  • Make sure that you have at least one vulnerable moment and try to show the softer side
  • Try not to curse and only make a Jack off hand gesture once or twice – – any more than that the date may come to a quick end

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