A California Girl's Guide to Dating in Chicago (pt. 2)

A Girl's Guide by Alessia

First Date DO :

That cocktail of butterflies, awkwardness and nausea that we're all inevitably sipping on a first date is never pleasant. Being a little nervous is good, because it means you might actually like the guy, but keep your cool.

When I was single, I tried to maintain the mentality of pleasant indifference. Like I wouldn't be fazed if he got hit by a bus in the middle of the date. Of course, this goes out the window if you’re on a date that is undeniably amazing. But generally, I tried to leave them guessing.

First Date DON'T : 

Don't be stupid.

The most common complaint I hear from my male friends is how unbearably dumb most girls are. I don't hang out with dumb girls, and I have a lot of girlfriends... so where are all these half-wits coming from?

My guess is perfectly intelligent females dumb themselves down because they think guys like it. Well, they don't. (And if they do, why the hell would you want to date guys like that anyway?) Worthwhile men want a woman who can mentally keep up.

Go read Newsweek or a book about monetary policy and the Federal Reserve before you go on your date, and be prepared for a second one to be planned before you're even done with dinner. I’m not saying you need to write for Forbes or be businesswoman of the year. If business and current affairs aren’t your thing, catch the highlights on ESPN. Last year I got asked out twice from conversations about the NBA lockout, alone!

The beginning of dates is always kind of awkward. What's the trick to cutting through that and getting to the "I'm on a really great first date" sparkle?

Be yourself and be honest - that's the best way to find out quickly whether your date is someone whose company you genuinely enjoy. J and I had an amazing first date. The best first date of all time – I’m serious. And looking back, it’s because we didn’t bullshit. We literally talked about everything on that date from the get-go – religion, politics, work, family – you name it. We were both open, and immediately felt comfortable.

I think the hardest part about dating is that you can never tell if the other person is feeling it. In the words of the late Whitney Houston ... how will I know?

Until J, I actually really enjoyed being chronically single and going on first dates regularly. It’s a full-contact sport! It can be tricky to get a good read, especially on the first date. But, nine times out of of ten, you'll know because chemistry is a two-way street. If there's any question, wait till the date ends. If they kiss you, you'll be able to gage the into-it factor. If they do something weird, like give you an awkward ass-out hug (which happened to me while on a date with a guy who only drank clear liquors – um, what? how about some bourbon?), you'll know they weren't into it, either.

Remember, the questions and uncertainty of dating are half the fun, so just enjoy it. Have fun out there, be smart and don't forget your sense of humor!

Alessia does Public Relations by day, and serves drinks by night. She is a Southern California expatriate and a newly minted catholic. She blogs at Un Giorno Da Leone and tweets here. She went on 12 first dates last year before finding the one

this is part 2 of 2 :  A California Girl's Guide to Dating in Chicago
it is the fifth installment of the feature A Girl's Guide


  1. so great! excellent reading material and great tips. "how unbearably dumb most girls are" hahahah perfect. and true.

  2. I so agree with the 'don't be stupid' advice - ugh, I hate it when smart, funny and lovely women dumb themselves down because they think that's 'what men like'. Also, I hate generalising about 'what all men like' - they're individuals, not a cloned group :) Great post, and very sensible advice!

  3. i loved these two posts - i find reading people's dating experiences so interesting! so glad you posted these - it led me to her blog, which i love!

    also - beautiful, beautiful photo at the top.

    - l

    1. Lauren, I think I needed this dating advice more than anyone! glad you enjoyed it.

  4. I defintely agree with the part about being open on the first date. Leave no stone unturned. I just heard that people ask an average of about 50 questions of the person theyre dating and in the end , end up saying "i didnt know he/she was" people should ask about 500 questions and talk about everything, because eventually its going to come up and its a good practice to not be afraid of conflict. Nice guys finish last


Thank you so much for commenting, Darling Reader! I read + love each and every one of them. (Anonymous commenting has been turned off due to robots)

ashore All rights reserved © Blog Milk Powered by Blogger