Memoir: 5 Good Things About My Worst Date Ever

I’ve never been a big dater; I’ve had boyfriends (and two girlfriends), but most of them I met through friends or at parties, and our romantic relationships grew out of being friends first. Actual first dates, complete with jittery nerves, fashion angst and awkward conversation aren’t my forte. The whole trying-to-get-to-know-someone-in-an-hour thing makes nervous, and seems way too much like a job interview that something conducive to finding someone I could fall in love with. But since I’m 34, single and looking to be in a relationship, I figured I should finally give online dating a try, so I signed up for OkCupid and HowAboutWe.

The results have been mixed, but I want to share five things I learned about a Very Bad Date that might help you in the dating jungle. I had proposed the date – a free comedy show at the Knitting Factory in Brooklyn – on HowAboutWe. The premise of the site is that you either respond to cool-sounding dates, or propose your own. This was a show I’d been wanting to check out for over a year, so I figured I’d rather do so with company. It took us about a month before we were both free. I knew very little about the guy, but was excited about the prospect of meeting someone new.

Well, my expectations were on the high side – the very high side, as it turns out – but I’m still glad I went on the date. Here are five reasons why:

1. Getting Dressed Up is Fun No Matter What

That day, I put on a flower-pattern Yumi Kim dress, got a manicure and pedicure and – something that’s a challenge for me – managed to fit all my stuff into my shiny new red purse, so as to make a good impression, rather than lugging my usual three to four giant bags. My date didn’t say a word about what I was wearing; now, he doesn’t have to, and maybe he wasn’t impressed, but a small compliment goes a long way. But wearing the outfit and matching bag, taking the time to make sure I looked my best, made me feel good even if he didn’t appreciate it.

Share This Post:
    • Word of Mouse Books

      Great post! Good for you not letting one sorry douchebag date get the better of you! It’s always amazing how some people just lack basic social skills.
      I think we’ve all had our share of bad dates and one other good thing about bate dates, you really notice the good ones when you get them! (Like cute compliment guy).
      Good luck!

    • Perry Brass

      As a friend, colleague, and admirer of Rachel (a lot), I loved reading about her bad date: it was like getting to peek into someone’s diary. However, as the author of The Manly Art of Seduction, How to Meet, Speak to, and Become Intimate with Anyone, I wanted to say a few things here that might be helpful. First, the most important thing in any seductive relationship is to understand intention, and intention is very difficult to ascertain in the “now or never” tensions of many first dates. Rachel’s date might have waited 5 minutes just because he was too nervous to follow her immediately. Same for the reason why he hardly talked, or sounded like a jerk or a dork: again, nerves showing. One of the best things you can do on a blind, website assisted date is compliment someone, as in, men LOVE to be told how good looking they are. So, saying, “You’re a lot better looking than your picture,” is a great ice breaker, and it makes guys feel like they are the ones being seduced. Men love this. Also, learning how to touch a man is very important, and I go into this a lot in my book. Most men are touch starved, and when someone begins touching them, in a reassuring, comfortable, non-threatening way, they basically cream all over themselves with happiness. Remember that on your next “bad date.”
      Perry Brass, author of The Manly Art of Seduction, now available as an Amazon Kindle book, and all other formats


      my worst first date could have gone worse but was still pretty bad. i’d met this guy at a party and we’d gotten along really well, despite finding out the next day he’d pretty much embellished a lot of things to impress me. nevertheless i gave him another chance after he explained that, and said he’d take me to go and see this road where the entire street is a party and the houses are all done up with lights. he was really hot and it sounded fun… it wasnt. sweaty hand, awkward silences on his end, ran into a drunk friend of his who asked if i was “the fifteen year old he’d heard about” (i’m nineteen, he was twenty-one). my date started stammering and tried to introduce me, but blanked on my name. and despite earlier asking if i was okay with him smoking (to which i replied i didnt mind in general but not around me thanks), ditched me to smoke with the drunk friend. guts. probably shouldn’t have given that second chance.