Are You a Pessimist or Optimist When Dating?

By Erika

If you know me at all, you know I’m a happy person. Like, sunshine and rainbows happy. Lollipops and daffodils happy. Springtime and gumdrops happy. And I’m an eternal optimist, truly believing that the glass is half full (maybe with a nice cabernet?) and that everything happens for a reason. But sometimes, just sometimes, I know that I can’t have too high expectations of people or situations because I may inevitably be disappointed.


Jeremy taught me a lesson very early on in our relationship: It’s better to be a “PSP” than a “DO.” What the heck does that mean? A PSP is a “pleasantly surprised pessimist,” and a DO is a “disappointed optimist.” My first date with Jeremy was on a Friday night. (I generally don’t recommend weekend evenings for a first online date, but it was the only night we both had available that week.) The next day, he e-mailed me to ask when I was free to go out again (yay!), and I suggested the following Tuesday.

In his response, he asked if he was getting demoted, going from a Friday to a Tuesday. My response back was that it was actually a promotion – I was giving him two dates in one week! He explained that he was hoping that was the case, but he’d kept his expectations low so as not to be disappointed. The lesson: It doesn’t hurt to go into new situations with no expectations because things can only go up. If you go in thinking that everything will be rosy, you’re setting yourself up to be let down. As optimistic as I am about life, I know that it was an important lesson to learn.

This lesson carries over to many aspects of dating:

Signing up for an online dating site for the first time. Remember, finding the love of your life takes time (and work), and Rome wasn’t built in a day.

Going on a first date. While you always hope that each one may be your last first date, just go in looking for great conversation and some things in common.

Going to a social event. It’s ok if your future spouse doesn’t sweep you off your feet at the event. Just go to have a good time and meet some new people.

Going to a wedding. I know they say weddings are a great place to meet people, and one of my best friends actually moved cross-country to be with a wonderful man she met at a wedding, but it rarely works out that way. If you’re going to a wedding solo, just enjoy the event, stuff your face with hors d’oeuvres, and partake heavily in the open bar if you so choose (but remember that too much may scare away that stud or studette sitting across from you at the singles table).

I’m a firm believer in looking at the bright side of things. But do so with caution: In new situations, I’d rather be a PSP than a DO.



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