Tag Archives: dating

The League + Marathon First Dates

Before we begin, I have a confession to make: I went back to online dating. But, I swear, it’s not what you think. Before rape joke guy and before my trip to Costa Rica in September, I heard about a dating app called The League. It was touted as being “exclusive” since there’s a waiting list, and it connects to both your LinkedIn and Facebook profiles to prove that you’re legit (no bots there!).

I joined aforementioned waiting list BEFORE I had forsaken online dating, so when the email came through two months later and two weeks ago that I had been “accepted,” I was pretty hesitant to say yes. Maybe, though, this was the universe’s way of saying, “Don’t give up on dating/online dating just yet!” so I hit the install button. I mean, I was grandfathered into this decision!

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The Fictional Narrative

Tonight I went to a live taping of one of my favorite podcasts, Why Oh Why. It’s a show about relationships and dating. I swear sometimes the host is inside my head saying everything out loud for her listeners that I am thinking (and sometimes writing about). When checking in to the show, you got to pick a name tag for yourself: Hi I’m Single or Hi I’m Not Single. There were also numbered paddles for the singletons. After you gave a brief bio to the ticket-taker, she was meant to give the matching numbered paddle to your “wingman”. And while this was actually a misnomer, the point was to match a man and a woman together so they could start chatting and, of course, fall in love.

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New Dating App: I’M READY (like, yesterday)

My best friend is a wife and a mother of three beautiful children. She lives in a giant, beautiful, old home in the historic district of Oak Park. They have a full-time nanny, a backyard, and loads of friends who also have nannies and backyards.

I love her children as if they were my niece and nephews. We play trains together, put together puzzles, and read books. We discuss their school days and I show them on the map where I’m traveling next.

While being auntie is great and I enjoy being able to “give them back” when they’re crying, snotting, or have a dirty nappy, I want more than just being AA (their nickname for Aunt Ashley). I, too, want to be a wife, mother, and owner of a home with a backyard. And while I love being an auntie who can do whatever I want when I want, including multiple vacations a year, date nights by myself to the movies, and trying out new dance classes that start at obscenely late hours (8:30?!), I fear this isn’t going to be enough for the rest of my life.

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Dating: A Stairway in the Dark

I liken dating to a stairway in the dark.

When you meet someone new, you walk into a dark, unknown space. You don’t know what to expect. You don’t know what’s inside. Eventually, you find stairs and you start to climb. The higher you climb, the more the excitement builds.

Sometimes the stairs end after one single step – a few words exchanged on a dating app – and you tumble over. It isn’t far, so it’s not a giant crash. You aren’t bruised at all.

Sometimes the stairs end after one story – a first date followed quickly by a ghosting – and you topple off the top of the steps. It hurts a bit, but you’ve been there before. Brush yourself off, walk out the door, ready for the next guy.

Sometimes the stairs are three stories high – a month or two of dating and then poof! When the relationship ends, the stairs end. You can never see where they’ll stop, but you can feel the fall. And this time it hurts. A lot.

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Filling the Void in my Heart

The literal female human heart weighs only 8 ounces, a mere .3% of the average female’s body weight. The figurative heart, though, makes up a much larger percentage of a female.

When I think about my life and the things I love most, my figurative heart is nearly full of contentment, happiness, and pride. I’d say my happiness level is at a steady 90%. With work, hobbies, volunteering, teaching yoga, and seeing family + friends, my general daily life is pretty darn great. And while I’d love to focus on these positives – hell, 90% is fantastic – I regularly lament that 10%.

Until only recently did I think that void could be filled solely with a loving partner and a family. Actually, it wasn’t until I started to formulate my ideas for this blog post that I fully realized I’ve previously filled that 10% and even brimmed over it on many, many occasions. Sometimes these moments are fleeting, including my “I love Hong Kong moments” and my “I love Chicago moments“, and sometimes they’re longer: when I’ve been in love and when I’m traveling. Also, now that I’m back from Hong Kong, whenever I see my friends from there, watch videos, or read articles about it, I am teeming with an overflowing love and gratitude for my years there.

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Pump the Brakes

Last weekend, I went on the perfect second date. It was astronomy night at Northerly Island, complete with night walks, telescopes, and nocturnal animals. He packed a picnic with all homemade items and cans of red wine. He picked me up. We laughed a lot. On a walk to watch the Navy Pier fireworks, the sky opened up and poured on us. We laughed more. Soaking wet, he told me I was still beautiful and then he kissed me for the first time. It was perfect.

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When he dropped me off at home, I took a full 10 minutes to celebrate in my head. This boy is a catch – smart, funny, attentive, has a good job, etc. etc. Then the doubting girl brain kicked in: “Hey, girl, wtf?! Don’t you go getting excited right now. He’s a boy. It won’t work. They never work out.”

“But,” I reasoned with myself, “we had SO much fun! He’s different. I feel different. He acts like he likes me.”

Girl brain: “STOP IT!”

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