The Bolder Life: The Dating Life

Dating. Is hard. And unlike a fine wine, it doesn’t get any better with age. Lately I’ve been hitting the dating scene a little harder than usual. I’m mostly in the market for a reliable date to be my plus one at the weddings of all of my engaged friends so I don’t have to deal with the awkward conversation that inevitably comes from the token single guy that gets assigned to sit next to me—the poor token single girl.

Dating takes a lot of patience. I curled my hair, put on deodorant, wore lipstick and only cursed three times on my last date—which I’d say was pretty successful on my end. Aside from watching my language, I also have to tone down the number of times I mention my adorable dog and work hard to stop treating a silent moment in the conversation as a challenge to see who can fill it first.

I might be a little ridiculous as a date, but when it comes to figuring out what to do on the perfect date, I’m not half-bad.

So this one’s dedicated to the token single people at the random guest table hidden in the back of wedding receptions everywhere. May these date ideas provide you with good conversation, and run just long enough to give you an out if you should need one!

Prospect Eats Food Truck Party
I used to be a picky eater, and would only order salad on dates (which can be justified but is kind of a no-no, girls). Now I’m just an indecisive eater and I freeze up when asked what kind of food I’m in the mood for. So—to avoid debating on which restaurant to go to, why not stop by the Prospect Food Truck party on Monday nights? Not only is there a variety of food and a little something for everyone, but it’s outdoors, and there’s live music. And if the date is going exceptionally poorly, there aren’t any walls to stop you from making a beeline for it when your date gets up to use the restroom.

Boulder Outdoor Cinema
This is one of my new favorite things to do in Boulder. Unfortunately, this Friday is the last time you can catch a movie in the parking lot behind the Boulder Museum of Contemporary Art in downtown Boulder. This Saturday’s flick is Pulp Fiction—which, unless you date hates Quentin Tarantino movies should work out fairly well and provide some good first date conversation. Grab some food to go from one of downtown Boulder’s tasty restaurants, a six-pack of some good craft beer or a bottle of wine and post up in the parking lot for dinner (and live music) before the show. Be sure to get there early, because the place fills up quickly, and don’t forget to bring your own chair. I mean, how embarrassing would it be if you had to sit on the ground…

Lyons Fork Beer Dinner
The Great American Beer Festival is coming up, and while I wouldn’t recommend attending the festival with a first date, for obvious reasons, I would recommend hitting up local beer events happening at breweries and beer bars near you. This year, the Lyons Fork is hosting a Maui Brewing beer dinner with 5-courses of amazing food expertly paired with craft brews from the Maui Brewing Co. Wear your cutest eating pants because no matter how polite and well-mannered you try to be, the food and beer at this event will be too good to leave sitting at the table.

Farmers’ Market Date
Yes, farmers’ market dates are a little cliché and borderline too cute, but if the date starts to go south, you can always use your newly purchased groceries as an excuse to go home. And if you go to the farmers’ market in old town Louisville, and the date doesn’t suck, you can always keep it going by heading over to Lucky Pie for a tasty cold beverage or make a trip to Sweet Cow if it’s not an appropriate hour to be drinking beer, or if desserts are just more you thing. Either way, farmers’ market dates are a good way to go.