Dear Captain Awkward,
I’m just going to jump right in. I have a first date coming up with a very attractive woman and I am freaking out a bit. We met on <Dating Website> and I feel like we gave each other really good message. Over the course of our conversation I learned her first name and the company where she works, which was of course all I needed to Google the shit out of her. Oh Captain, I normally have anxiety issues in general, but what I found has escalated this to Code Red. Turns out she went to <Very Snooty All Girls Boarding School in New England> and then attended <Very Prestigous University>. We work in the same industry, but she works for <Big Time Corporation> in <Iconic Skyscraper That Gets Blown Up in Movies>, and her job description is what essentially would be my boss, if not one level higher than that. She does tons of awesome charity work. She has been featured in newspaper articles about “Top 30 Under 30” and “Most Eligible Singles.” None of this (other than her employer) has been brought up in conversation, only through my Google snooping.
In short, I am not ready for this girl’s jelly.
Don’t get me wrong, I am a smart guy and enjoy my job and life (most of the time), but I feel like she has her shit together way more than I do. I know she lives in a nicer place than me, makes way more money, etc. And I know those are bullshit material things and no way to judge a persons worth….but I worry how she is going to look at me when it becomes clear she has accomplished so much more. As one of my friends said when I was lamenting my “problem” to him – “Maybe she’s really attracted to slovenly oafs?”
I feel like I should mention that she was the one who messaged me first. Contacting me out of the blue and praising how much my profile made her laugh and wanting to know more about me. Like I said, our messages have been great and when I asked her out for drinks she quickly accepted. I realize this is a good sign, but if anything it has made my stupid brain worry more. Like “There might actually be something here DON’T BLOW IT.” (or as much “something” there can be after a few dating site emails).
I know you’re just going to tell me to “be myself” and worry more about whether she’s the one cool enough to be with me. But is there any advice you can give on how to be less of a spaz about this and just let go?
Even The Beast Had An Awesome Castle
Okay, Beast, your letter was so personable and funny that it had me Googling the ethics of an advice columnist asking out someone who writes in for advice (Good news, everyone, there are no rules about that), so I’m pretty sure you’ll do fine.
Snooty girls from New England need love, too.
I know many brilliant badass women who are great at stuff. You’ve all met Commander Logic, yes? Basically, all of our friends are as awesome as she is. And they are all unique fabulous creatures and there is no one way to impress them or get to know them, but I can tell you one secret peeve/awesome thing that comes up over and over in discussions of online dating* we’ve had with each other:
- A guy who gives good email and then segues into making plans in a way that is effortless, like, want to do something Tuesday? Sure, ok, let’s meet at <place/time> = SEXY.
- A guy who must trade 17 emails in order to make plans, and keeps using the words “Whatever you want to do is fine” and confirming and reconfirming and offers everything a an option, like, “Well, I know we said Saturday but I could also do Sunday OR Tuesday…if you wanted...”= ANNOYING. Sometimes we rally and go on this date, but it is doomed from the get-go.
- I wrote this in 2005, and while I think the section on Cafes I Have Loved is overwrought and pretentious, the premise that The Coffee Date Almost Never Works is basically sound.
So that is my advice for you: Be able to suggest a solid plan with confidence. If she suggested the plan for the first date, roll with whatever she suggests and have a good time and know that for the second date you’re the one who makes the plan. No need to go overboard – you’re not Richard Gere taking Julia Roberts to the opera in Pretty Woman – but being able to come up with a cool meeting place that is relaxing to be in and where you can hear each other talk where there is something to look at or do (or that is also walking distance from a restaurant or movie theater or gallery or some other place that you can spend some time if the date is going well) is essential. Bonus points if it’s some place that you love or have a personal connection to or are really curious about and can explore together. It’s less about impressing her with how hip you are than about knowing what is a good space for hanging out and connecting and making everything really easy and relaxed.
I feel like a lot of brilliant badass women comment here and will be full of good suggestions for you. SexyTypewriter, get in here and tell this guy what’s what!
*True story: There was a year we were pretty much all on <DatingSite> at once and nearly broke the city of Chicago with our awesomeness. Also, if you liked one of us, you liked all of us, so there was much comparing of notes and mocking of triflers. Long live the Shadowy Dating Juggernaut!