Dating for Pleasure

Kimberly,

I have been following you and your stories for a long time...it seems like you’re always going on dates...I have not been asked out on a serious date for over 2 years now...I get men 20 years younger or 20 years older asking me out...i have tried dating websites and everything in between...how do u get so many dates? 

Signed, 

Just Curious

Dear Curious, 

First of all, half of the dates I go on are hardly dates at all. Sometimes, I'll just meet a guy out somewhere and we decide to continue hanging out after the party / beer garden / improv show / christening etc. I'm not even kidding. I've met people randomly at all these places. I meet guys everywhere, because I always have fun doing whatever it is that I'm doing. I recently met someone while volunteering at a local farm. I met someone in the cereal aisle at stop n shop. I met a guy on the train. Scratch that - two guys! I am always meeting friends of friends, and people are constantly keeping me in mind to introduce to some "great guy" they know. The secret is, I'm not afraid of admitting that I'm single AND LOOKING. Sometimes, people assume you're single by choice. They think you're a strong, confident, capable woman who doesn't need a man. And to be clear: I don't NEED one. But I WANT one. I know that I love being social and going out on dates. I know that I want to be married and have children someday, and that requires a male in my life. When you allow people to see that you want to date for pleasure, you'll be shocked at how the guys just kinda come out of the woodwork. Also, I'm not shy at all about walking up to a total stranger and telling him I think he's cute. No joke, I have shocked friends when we're out by approaching a hot (yet inevitably nerdy) guy and striking up a conversation about whatever is relevant at the time. Usually, I have a back up witty line in my pocket, like "Hey my friend bet me $10 that I wouldn't come over here and talk to you" or "My friend bet me $10 that you're single and I said there's no way cause you're too cute to be single!" That way, you have an automatic in and you find out in the first five seconds if they're available or not. I flirt with guys every place I go. The farmer's market is the best because you already know you have something in common --- healthy eating and a passion for the outdoors. Fairway or Trader Joe's or Whole Foods are excellent alternatives in inclement weather. I go on group trips like whitewater rafting and hiking and game nights and trivia, just to have something to do so it's not awkward when you're sitting across the table from each other at Starbucks and there are lonnnnnng pauses. I am also online. I almost forgot how terrifying it was going out with someone new! (Almost!) I think that the key online is not being afraid to be your most authentic self. If a guy doesn't like you, he doesn't have to message you, but if he does like you, you'll both know that he likes the REAL you, not some watered down or trumped up version of your best PR self. Don't be afraid of details. Guys like specifics. When it says "what is your typical Friday night like?" I actually list the last 5 Friday nights. At a low key pub with my girlfriends, going to bed early because I'm running a 5K the next day, chilling in the Hamptons with a bottle of wine and a great view of the water, on a road trip to New England, eating a delicious sushi dinner and catching up catching up with colleagues etc. This lets them know that I'm active, I don't sit home watching movies, eating Oreos and doing my laundry (I save that for Wednesday nights!) Just because I'm single doesn't mean that I don't get to have a life! I don't say yes to every guy who asks me out but I do try to be adventurous and take a chance on someone who might surprise me. Two of my girlfriends married guys they didn't think they would like online but were pleasantly intrigued when they actually went out. So you just never know who's gonna be around the corner. I dress up every day like I'm about to meet the man of my dreams. It's worth the three seconds to swipe on lip gloss before I head into the supermarket, or the post office, or the library. You never know who you're gonna meet. Hope this helps! 

Hugs, Kimberly