I asked 4 women to go on 'lady dates' — here's what happened

Nov 28, 2014 at 6:00 p.m. ET
Image: Maciej Noskowski/Getty Images

I am not a naturally shy person. My husband likes to say that I've never met a stranger. Still, making new friends is not as simple as it once was. For five and a half years, I worked as a magazine editor with a load of female colleagues — the entire office was our "water cooler." Some weeks I spent more time with them at the office than I did at home.

When my husband and I moved out of the city to be with family after our first child was born, what I didn’t account for was how difficult it would be to transition out of having that daily dose of female companionship. Of being able to talk about anything and everything with my girlfriends.

We moved back to the city a year ago, and working my way back into old social circles has been slow going. Sure, we still talk and we meet up for lunch dates, but we're not in that place we were — the place where we are inherently silly with each other and turn a quick meeting for coffee into a three-hour chat fest.

The goal of this challenge: to uncover a few more soul friends — women who I connect with instantly. Women who, when something big or terrible or shocking happens in my life, I want to call and spill about whatever is going on with me.

Date number 1: Freelance Writer

Freelance Writer has a very dry personality, and I've resisted accepting any of her invitations to go out socially for fear that it might affect our professional relationship.

Do you remember that scene in Sex and the City when Carrie and the girls are spending a few days in the Hamptons? A cute doctor asks Carrie out at a book release party, and he finds her on the beach to ask her out. He's handsome, he's funny, he's a doctor — he's good on paper, the girls say.

Freelance Writer was the platonic female personification of good on paper. Sure, we have a ton in common — we are both writers, there are some overlapping friends in our social circles, we share a love of seaweed salad... but there just wasn't a whole lot of chemistry.

At one point during our lady date, she said "YOLO" to me in that peculiarly flat affectation of hers, and it was altogether too bizarre and uncomfortable for my brain to process. I wasn't crazy about the way she spoke to our waiter (who was fantastic), either.

In short, I don't foresee her being a best friend. All of my best friends to date I shared an intangible but powerful connection... one that is nearly always evident right away. With Freelance Writer it was conspicuously absent.

Date number 2: Aquarium Mom

A few months back, while at the children's museum with my 3-year-old daughter, I hit it off with the mother of the little boy my daughter was playing with. Before we left, I pulled out one of my business cards, handed it to her and told her to call me anytime she comes back this way and wants to meet up. She texted me a few weeks later, but I had family in town and couldn't steal away.

So I texted her back. It felt a little awkward since over a month had passed since our last exchange, but I really wanted to make it work — and I'm so glad we did.

Sitting next to her at the aquarium, she was every bit as warm and genuine and fun as I remembered. She, a stay-at-home mom, and her husband, an engineer and craft beer enthusiast, live about 15 minutes away from us in a smaller suburb of the city... definitely close enough for frequent get-togethers. Plus, when she told me she is equally obsessed with Fried Green Tomatoes and The Walking Dead, I knew I'd found a kindred spirit.

Bonus: Our kids get along great — her older son is my daughter's age and her younger son is my son's age — and her husband sounds like someone my husband could absolutely kick back and have a beer with.

Date number 3: Friend’s Girlfriend

I've known Friend's Girlfriend for, wow, probably 10 years now. When she began dating one of my closest guy friends in college, I didn't get it. No one in our circle of friends did. I feel mean for saying so, but I've always thought of her as being vapid. And moody. But they're still together, and she has been asking forever and a day if we can get together to grab a bite to eat or do something social.

I decided to bite the bullet and give Friend's Girlfriend a call. After all, if my buddy loved her so much, surely there was something of merit. And, you know, I'm not quite sure how it went. The conversation was pretty decent. We know a lot of the same people, so we may or may not have indulged in a little garden variety gossip. We also discovered that we both play volleyball recreationally, which surprised me.

She's a very hard person to read. I can never tell if she is having a good time. She's a bit awkward and she's not outwardly bubbly and happy, so I'm not sure how to take her. I haven't decided yet whether I'd want to hang out with her again one-on-one. If I can get past her awkwardness enough to go out with her a few more times and get her to let her guard down, I might find that there is more to her. I'm open to trying to find out.

Date number 4: Online Connection

I'm currently doing a multi-week web seminar for female entrepreneurs, and I've connected online with several of the women doing the summit who also live in this area. One of the women really intrigues me. Everything from the way she dresses to the website of her company seems so hip to me, but in a way that is effortless. She doesn't seem to try too hard... she's just herself, and herself happens to be this incredibly cool chick.

She seemed super excited when I messaged her about meeting up for coffee, and we decided to meet the following day. But the next day, as I sat sipping my chai latte, 10 minutes came and went. Then 15. Then 20. Every time the door opened, I waited for that moment of recognition.

Only, it never happened. Womp, womp. I felt like Meg Ryan's character in You've Got Mail.

I messaged her to make sure she was OK and a few minutes later received an apologetic response. Her son was sick and she just spaced. I'm giving her the benefit of the doubt, because I have kids and I know how that goes. Nevertheless, it was mildly embarrassing to have reached out and then gotten bailed on.

I still sincerely think Online Connection and I could hit it off. My worry is that she may feel awkward enough to dodge any make-up date I might suggest, thereby never giving us the chance to get to know each other outside of the webinar. And I certainly don't want to be the creeper who keeps trying to coerce her into a friendship she isn't sure she has time for or interest in. For now, I'm leaving the ball in her court.

I'm not sure why it took being tasked with this assignment for me to reach out to women in this way. I didn't find the asking awkward so much as those first few moments after meeting. It was almost like being on a real first date!

And, like a real first date, it's honestly kind of a crap shoot. There was no way to predict who I would end up hitting it off with. Some of the women who seemed to be "logical" fits (same career, shared hobbies, similar life stage) proved to be total duds in the chemistry department. Others who seemed like long shots actually left me with the hope of a lasting friendship forming.

So far, I've only set up one follow-up date. Next Thursday, Aquarium Mom and I have plans to rendezvous once more at the children's museum. Maybe I followed up with her first because where she is in her life most closely resembles where I am. We are both in our early 30s, our kids are the same ages, our husbands are the same ages. It feels... easy.

If there's anything I learned from my other lady dates, though, it's that you'll never know how you really feel about people until you put yourself out there. And I can truthfully say I'm looking forward to doing more of that in the future — even if it means the occasional coffee shop stand-up.

This post was sponsored by Sanuk. Never uncomfortable.

More dating articles

What Tinder dating is like when you have a disability
What guys say vs. what they mean, as told by Ryan Gosling GIFs
8 Awkward stages of a first date, as seen in GIFs