Making the first move leads to no regrets

Kirstie Taylor

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I watched my friend's eyes widen with excitement and nearly burst from trying to contain herself.

“Yes!” she exclaimed while sitting across the table at our favorite cafe, “He’s so sweet and kind. Ask him on a date!”

We had a mutual friend who I’d known for a few years. I’d been between boyfriends so often or on a self-imposed dating hiatus that I’d never took notice of how sweet, cute, and all-around great guy he was.

But my friend’s reaction confirmed that I was making a solid choice.

That’s the moment I decided to ask my now-boyfriend out on a date. Well, he didn’t exactly know it was a date. He believed me asking him to grab brunch — which was our first time hanging out alone, without anyone from our friend group — was simply because I wanted to catch up.

Little did he know, I was making the first move.

It’s funny to look back on now. My boyfriend is outgoing yet reserved when it comes to all things romance. I’d only once see him with a woman in the years I’d known him prior, and even then, he was pretty mum about her.

Since our first date, I’ve asked my boyfriend several times (because I’m annoying like that) if he ever would’ve asked me out if I didn’t ask him.

“Probably not,” he replied. “Not because I didn’t find you attractive, but I didn’t want to make things awkward with our friend group if you weren’t interested. Plus, I never would've thought you’d say yes.”

In life, you have to take hold of the proverbial reigns. I’ve found that to be true in a lot of things:

  • I pitched my book to my publisher, which is how I landed a book deal.
  • I reached out to a successful freelance writer who helped me build my career.
  • I sought the professional help I needed to pull myself out of the deepest episode of depression I’ve been through.
  • And then there’s my favorite one: I asked my boyfriend out on our first date.

That last point might not seem like a big feat, especially if you’re a man. You’ve been taught that making the first move is your biological duty. And, to give you credit, there are still plenty of women out there who don’t make the first move. Essentially, it was the only choice you had.

But for women, things are different. We grew up watching Prince Charming save Cinderella. The TV shows we consumed were filled with young high schoolers waiting for their male crushes to ask them on dates.

Most of us were taught not to be “bossy,” which essentially meant not having an opinion or controlling things. Forwardness wasn’t rewarded in nearly any aspect of our life aside from how we dressed (which is a whole other topic).

This article is two-fold. I want anyone who reads this to understand how important it is to make the first move, applied to whatever aspect of their life is relevant. But it’s more specifically for women who still believe that love will happen to them, not because of them.

Before dating my current boyfriend, I decided to try a yoga studio near my Santa Monica apartment. But the class ending up being hot yoga, and I was poorly prepared, having only drunk a cup of coffee before.

Halfway through the class, I saw my vision start to blur. Rather than tough it out and potentially pass out in front of many strangers, I quietly B-lined it for the reception area. Once in the cool air, I felt my body regain full consciousness.

That’s when I realized I wasn’t alone. The guy working the front desk was looking at me and asked if I was OK. He gave me some water, and we chatted until the class ended so I could grab my yoga mat.

This guy was charming, with a yogi’s body, but, more importantly, he had a kind, caring way of talking to me. Before I realized it, people started flooding in for the next class. Once mine ended, I grabbed my mat and left to walk home.

I immediately called my friend, “This guy I just met was so cute and sweet. I wish he’d asked for my number.”

“Call the studio and ask for his! I’m sure he’s still there,” she reasoned.

After a lot of second-guessing myself and rehearsing what I would say, I rang up the studio. Lucky for me, the guy answered. I explained who I was and that I’d love to grab dinner with him sometime.

“Wow, I’d love to,” he replied, “I’m so glad you asked me.”

While he and I didn’t end up lasting past two dates, I felt empowered at that moment. Instead of expecting the guy to ask me out, I’d done it myself. Had I never called the studio, I would’ve been left to wonder what could’ve been.

You can’t sit around waiting for life to happen to you, especially when it comes to dating. That’s how you end up dating people with bad intentions and feeling like you’re lucky to have someone, anyone, ask you out.

How I see shooting your shot is this: you have nothing to lose. If the other person says they’re already in a relationship or just isn’t interested, then you’re back to where you were. But at least by asking, you have an answer.

This applies to everyone: friends, that cute girl at the coffee shop, or an old co-worker. If there’s someone you’ve been waiting around to ask you on a date, do it yourself. You’ll not only have an answer about how they feel, but you’ll be f*cking glad that you took control of things.

I believe the best things in life come when you ask for them precisely because that’s true for me. I wouldn’t have the career and relationship I do today if I didn’t go out there and get them.

Rejection can be scary but the way I see it is wondering “what if?” is much scarier. I’d rather know, even if the answer is a no. Living life with regrets is something I try to avoid, even if I feel terrified and uncomfortable in the process.

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Dating, relationship, and self-love writer. Helping the hopeless romantics of the world feel more hopeful.

Los Angeles, CA
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