As seen on: The Stripe

Hi friends! Clara here again, your resident dating guru.


If you had told me five years ago that I would now be considered a dating “expert,” I would have laughed in your face. But then, in the spring of 2014, the relationship I thought would lead to marriage came to an end, and I found myself alone for the first time in almost seven years. I knew in my gut that breaking up was the right thing to do, but it was still terrifying. How would I ever find love again, another partner, another best friend?

The apps were all the rage, but after experimenting with a few, I hit a wall. It wasn’t that I thought they were hopeless (I did later master them) — they just weren’t right for me. Despite all the claims of impossibility, I was determined to meet people in person. And not in a way that required going to bars (that would disturb my 9:30 pm bedtime) or being “on” all the time. I was determined to weave the effort to meet my future partner or simply someone great to date into my everyday.

It took some major missteps, some laughable moments, and some very poor landings, but I finally found my way. I started to meet people in coffee shops, on the subway, in line for the bathroom at restaurants and more. My options felt endless! I not only mastered the technique, but as I’d hoped, it lead me to my person, my partner, my “let’s do life together” teammate (we met in yoga class, btw).

Here’s an overview of my approach:


When I first start working with clients and broach the subject of meeting people in person the response is often, “But I can’t just go up to someone!” or “I really don’t feel like going to bars.”

Chill my dear, chill. We’re not there yet. We’re going to ease in nice and slow, by first and foremost getting your head out of your phone. It’s time to stop scrolling Instagram (just for a little) and start to get really observant about your everyday. And I mean really observant. Does anyone or anything catch your eye at your coffeeshop, on your walk to work, at the gym or on the subway? Of the people you find attractive or intriguing, what do you notice about them? What gets you excited and curious and wanting to know more about them? Start tapping into the people that make you pause.


Every time I order a coffee I make a point, before even ordering, to ask the barista how they’re doing. And not just mutter the words but really ask. Why? Because they’re a freaking human being that’s about to get me my coffee. I’m not here to guilt you into chatting up your barista (well, not exactly). I share this example to show how ludicrous it is that we don’t acknowledge the people we interact with—even if they are strangers— in our everyday.

So for the next few days, I’d like you to practice doing just that. It doesn’t have to be with someone you find cute. It can be with the person behind you in line at the grocery store. Perhaps you compliment their shirt. Perhaps it’s with a coworker you don’t speak with very often or at all. Even just smiling at someone and acknowledging their existence is sufficient. It doesn’t really matter. The point is to practice being friendly with humans you don’t know.


Aaaaalright, so you’ve been taking in all that surrounds you and hopefully smiling and complimenting strangers left and right. You may have even started to experience how easy it is — how one small gesture or word can lead to a meaningful interaction. Hopefully you’re feeling a lot more comfortable striking up a conversation with someone you don’t know now, but if you’re not there yet, feel free to linger in this phase a bit longer.

Now, take a step back for a second and imagine: what if you were to do that with someone you found attractive? I know. I KNOW. Feels terrifying, right? Don’t worry about that for now. For this week I just want you to play with the possibility. Meaning, when you see someone you find attractive, acknowledge you could strike up a conversation. The possibility does exist. Meaning, there are people out there in your everyday life (not in an app, at a bar, etc.) that you find intriguing.

This period is not about conjuring up the courage to ask those people out or figuring out if they’re already partnered up. Instead it’s about noticing the moments where the opportunity does exist — where you cross paths with someone you’re deeply intrigued by and want to know more. All you have to do is notice it.


You know how I said the last few days weren’t conjuring up the courage? Now it is. But let’s step back first…

When I first started engaging with guys out in the real world and attempting to ask them out or lead the conversation that way I had approximately one million fears running through my head: What if he knows I find him attractive? What if he has a girlfriend? What if he doesn’t respond? How do I even freaking ask him out?!?! And then some. I.was.a.mess.

I calmed myself by reminding myself of the following:

  1. I am a human. He is a human. It is natural (even if we don’t know each other) for humans to converse.

  2. I am not wearing a big flashing sign over my head that says “I THINK YOU’RE CUTE” so just because I ask him what he’s reading or drinking or doing doesn’t mean I’m giving anything away.

  3. This interaction will not kill me. I repeat, this interaction will not kill me.

  4. If we do get to the point where I ask him out and he is in a relationship, so be it. Remind yourself of number three. High five yourself for being bold.

The first time I mustered up the courage to talk to a guy I found attractive felt like pushing myself off a really big diving board. I was so close to chickening out and then, at the last second, went for it. I decided the outcome didn’t matter. Honestly, I just needed to get this over with.

And I did. Like anything, the more I did it, the more comfortable I became. There is absolutely no way around being vulnerable when it comes to dating and relationships. In person, apps, friends of friends – it’s all going to feel uncomfortable and scary at times. The real key to meeting people in person is simply becoming more and more comfortable with that reality. And yourself, of course, but that’s a whole other topic :).

I hope all of this was helpful! If you’d like to go deeper on any of this, or something else related to dating and relationships, I’d love to work with you! Shoot me a message on Instagram or email at

Clara Artschwager