Meeting People in Person.

Meeting People in Person.

It’s Friday afternoon so Clara is back again with her second dating post. (Read the first one here!) I could not love today’s post more. I have to admit that I am pretty terrible at this – approaching a stranger is still pretty scary to me. Clara met her boyfriend in yoga class which I think is so cool. All of her advice is spot on… she breaks talking to new people down into easy steps which make it seem so much less intimidating. Even if you’re not single I think this is a really good read as talking to new people is a skill we all can definitely improve upon. You could just as easily apply most of this advice to making new girlfriends!

A huge thank you to Clara for sharing her wisdom with us (and if you have a dating question for her for a future post, please email me or leave them in the comments below.)

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:

Step 1: Get Curious

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.

Step 2: Get Friendly

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.

Step 3: Play with the Possibility

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.

Step 4: Go For 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

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  1. It’s always interesting to read about the dating scene nowadays, since I’ve been long out of touch with the dating game (I’m in a long-term relationship). I don’t think I’d survive, haha!

    Charmaine Ng | Architecture & Lifestyle Blog

    11.30.18 Reply
  2. Aw love this advice! I’ve always been very, very bad at approaching people! I’m way too introverted haha! I’m grateful to be in a relationship, although I do think there is a lot of excitement in the dating world!

    11.30.18 Reply
    • It’s such a scary thing to do! I assure you you’re not bad :). We’re all just not used to it!

      12.1.18 Reply
  3. This is seriously the best dating post I’ve read in so long and kind of exactly what I needed. I had a similar break up experience to what you mentioned a few years ago (with someone I met in person). Since then, I had been using apps but recently stopped altogether because it just wasn’t working, didn’t feel natural, and honestly wasn’t enjoyable at all for me.

    I’ve been committed the last few months to really figuring out what I want and also just spending time doing the things that are important to me and making new friends. In the back of my mind, I’ve been thinking about how I want to meet someone organically in person again but have been curious as to how that would happen since the world is so consumed by their phones and dating apps. This step-by-step outline was genuinely so helpful, so thank you SO much 🙂 I feel a lot better.

    briana |

    11.30.18 Reply
    • I am so glad, Briana! You’re well on your way and I love your positivity. Much love, Clara

      12.1.18 Reply
  4. Susan:

    Clara! (and Grace!)–I’m really enjoying this series! I’ve been seeing my current boyfriend for almost 6 months (the first real relationship I’ve ever had at 29!) and yes, we met online, but I really appreciate these tips and I’m excited for what’s to come! Because every day is new and I don’t always know what I’m doing so reading all of this advice really helps! and definitely is a great reminder to chat it up with everyone around you too! You never know when new friends will come into your life!

    12.3.18 Reply
    • That’s so great to hear, Susan! I find the advice helpful in a variety of scenarios, too. This is good to know as well for potential content…perhaps we’ll do some more relationships focused content!

      12.3.18 Reply