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When it comes to dating, things are never as easy as they should be. From trying to figure out where to meet nice guys to navigating a budding romance, dating can often feel like too much to handle on your own. So we asked some smart and savvy women to give us their takes on modern dating.

Despite what we all tell ourselves, there really are so many opportunities to find love. Unfortunately, too often we miss them.

Most of the time we miss a chance at a real relationship because we are looking down at our phones, too inhibited to say hi, or too nervous to take the next step and exchange numbers. In fact, Craigslist has it’s very own outlet for just such lost opportunities called Missed Connections. Some of them are gross, but most of them are really sweet. Check this one out from Fourth of July weekend:

“I was in my old Chevy Tahoe, heading out of the city after the fireworks; you were on the street watching the locals shoot off fireworks. My dog was in the back seat. We spoke for a few minutes before the light turned. You are stunning and have a great smile and sparkly personality. Would love to take you out some time if I can find you!”


There are all kinds of misconnections that cause us to sometimes look back and wonder "what if." We may not be able to track them down on Craigslist—and maybe we don’t want to—but there is value in reflecting a little bit on what exactly was missing.

So ladies, my question for you is why didn’t the relationship take off, be it long term boyfriend or just a couple dates, and what did you learn from it?


Maddie: Stuck in the Fun and Flirty Stage

I’ve had such great back-and-forth with some guys—over text and in real life—that I was sure a grand romance was to come. We’re hilarious together. Soul mates, right? Unfortunately not.

When it came down to it, I couldn’t get deep with these guys. It was as if our intricately woven web of connection, spun with snappy comebacks and on-point pop culture references, was threatened by deeper personal sharing. We could talk about serious issues in the abstract, sure, but when it came to our personal lives, neither of us were really as comfortable as we had been when we were quoting YouTube videos. Despite hoping these fun and flirty relationships could become something more, I never challenged the status quo of witty quips and impersonal theory. Turns out your ability to spin one-liners does not a solid relationship make.

When I finally stopped letting the comfort of emotional distance get in the way of a possible romance, I got hurt a few times. But it was worth it to know that when it came to connecting with the other person on a meaningful level, I had tried. Intimate connection is a two-way street, so if you find yourself too wrapped up in your witty persona to let someone new into your personal life, test the waters by sharing a piece of your heart—and see what happens.

Grace: Netflix and Opting Out

As the resident single friend of my group, I’ve gotten a little too used to queuing up Netflix on Saturday nights instead of actually going out to socialize. But this is more than just being an introvert and needing a chill night like everyone does sometimes. Nearly every night, I opt out of meeting guys. I’ve always prided myself in my peaceful single life free of heartbreaking “what ifs,” when the fact is there are no missed connections to be had. Not saying hi to the guy across the room is one thing, but not even trying is another.

Needless to say, I’ve gotten a little tired of watching all my friends enter relationships and being inexplicably upset by their happiness. It’s only taken me a couple years of cynically proclaiming that all the good ones are gone to realize that I can’t just go around making these depressing and seemingly unsupported claims without at least trying to prove myself wrong. Moral of the story: If you’re lazy and skeptical like I was, you’re missing out. Take a chance—open the door to possibility by making yourself available. You never know!

Nadine: Focusing Too Much on the Red Flags

I met a guy once who I had some interest in, but I wasn't all in. After the second date, he asked me where I saw this relationship going. Sure, I liked him, but I wasn’t sure if I wanted to commit to him. I mean, what if we started dating and I realized he wasn’t what I wanted? I spent a week filling my mind with reasons to say no, but I never considered reasons to say yes. Maybe this was my logical reasoning telling me he wasn't the right guy for me, but maybe it was just fear getting in the way of something that could be great.

He was hurt by my hesitation to give a definite answer and eventually stopped talking to me. This hurt me as well because I had seen real potential to be at least friends. Even though this missed connection ended badly, it taught me that I shouldn’t be overly cautious about giving a relationship a chance. When I met my now boyfriend, I was still hesitant, but I took the plunge, and I definitely don’t regret it.

Emily: One Too Many Good Excuses

My missed connection still haunts me. I was escaping the city for the weekend to visit family. As I boarded the train, I was puzzled by the lack of empty seats. I walked through the aisle, and I passed a guy that looked around my age. He smiled at me but I kept walking, hoping to find two empty seats—you know how it goes. As chance would have it, I had no such luck, so I turned around and found that friendly-looking guy, still sitting there.

He was so kind and unlike anyone I had met. We ended up chatting for the entirety of the three-hour train ride, which resulted in exchanging numbers. He got off before me and said that he would be in touch when we were both back in the city. He called me two weeks later. Long story short, we went on a few dates and ended up dating for a few months. I was kind of amazed. It was the perfect story....

And yet, while he had every quality I could ever want in someone I would marry, circumstances got in the way. I had just moved to New York City and needed to get my bearings. I wasn't settled in my own life yet, so I didn't feel like I could fully commit to a relationship. The truth is, the timing just wasn't right. Sometimes unavoidable circumstances in life get in the way of a chance for love, and it’s important to be at peace with these limitations. Still, as I write this, I often wonder if there is still potential with my “missed connection”—or if I should have made the time to make it work.

Photo Credit: Jess Hunter