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How I Went From Awkward Teenager to Offline Dating Coach

It was the most dreaded time of the day: lunch time.

That meant walking into a huge room full of hundreds of people, all of them judging me, and hoping there was still a spot left at a table so I wouldn’t look like a loser. I really hated middle school.

Since then, life has thrown curveballs a lot bigger than worrying what a bunch of 13-year olds thought about me. But at the time, facing that midday meal every day was almost enough to make me lose my appetite.

So how did I go from being afraid of the lunch room to becoming an offline dating coach who helps women meet men in the real world?

It’s all in the baby steps – taking a conscious effort to push past your comfort zone in small ways at every opportunity. Because social skills are actually a muscle, the more you work them, the more toned they’ll get – and the more attractive you’ll be to other people.

Looking back on the journey of breaking out of my painfully introverted shell, I saw three distinct stages of conversation skills that I unknowingly mastered along the way, each building on the one before. And it all started with the lunch lady.

The art of small talk

The first stage came during that middle school lunch room – and tennis practice, and algebra class… Basically, every time I had to walk into a new environment by myself, I’d feel some level of anxiety.

Until I spotted a friend on the field, or the teacher finally began talking, I’d usually sit by myself feeling a pressure to join the random conversations of classmates happening all around me. But I didn’t know how to do it without being totally awkward.

So, I started practicing on people who were “safe”: my tennis coach, teachers, the woman at the lunch room checkout counter. Growing up with older parents, I was more comfortable around adults than kids my own age anyway, so this was the perfect way to begin putting myself out there in a not so scary way.

I’d hang around my tennis coach before practice and chat with him about school projects. My math teacher always made it a point to ask me how tennis was going. The lunch lady and I started a running joke with each other one day after I accidentally tried to pay with Canadian money instead of US.

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The results of these random interactions were small, but meaningful. Once I started building rapport and confidence with adults, I realized it was easier than I’d thought to chat people up about everyday topics. And, it was actually kind of fun.

If small talk with random strangers feels uncomfortable for you, start challenging that mindset by creating short conversations with the people who are “safe”: the bartender, the doorman, the grocery bagger. Anyone you encounter in a service industry who’s on the job.

Ask how your waiter’s day is going and look him in the eye so he can tell you’d really like to know. Tell your pharmacist how excited you are about your camping trip to Wisconsin this weekend. Make it a point to say hi to every taxi driver as soon as you open the door, then flash a huge smile.

Every one of those people are being paid to provide you with a service and to interact with you. And when you talk to each of them like a fellow human being, as opposed to someone who exists only to serve others, you might just make their day.

The art of making friends

After conquering my conversation anxiety with adults, the next phase was mastering the art of making friends my own age. This played out in a big way when I went off to college in California.

At first, I clung to the most convenient group of people: my roommate and her friends. But being the only introvert in the group became exhausting. I knew I needed to find friends more like me who preferred in-depth conversations over hanging out in huge groups at basketball games.

Using an authentic strategy of simply being nice to everyone I encountered, I started meeting other students in my dorm, my classes and at parties. I took the pressure off myself to have every conversation result in a specific outcome, and simply enjoyed each moment for what it was.

I stuck with speaking mostly to girls, since I was still a little shy in the guy department, keeping in mind the worst that might happen is they weren’t interested in talking to me – and the best that could happen was I made a new friend.

I’d compliment another girl’s scarf and ask her where she got it. Or ask the girl across the dorm hall to come grab lunch with me. I found the key to making new friends was simply taking what I’d learned with having random small talk chats and adding a little follow-up action.

If you feel comfortable engaging strangers in small talk, but aren’t quite sure how to take things to the next level towards making a new friend, start by creating interactions with people who share a common interest, then take action by asking them to get together again in the future.

Volunteer at a local shelter or food bank and talk to other volunteers as you work. It’s so much easier to have a natural conversation when engaged in an activity together, as opposed to sitting across the table from each other interview-style.

If you’re new to a city, accept every single invitation that comes your way – even if it’s “not your thing”. You may not click with the person who invited you, but chances are if you simply show up, you’ll find someone at the event you feel a connection with.

Then, after you’ve found that person, take action. Toward the end of the event or conversation say something like “Hey I’ve gotta run, it was great talking with you. We should grab coffee sometime.” Wait for them to agree and then ask “What’s your #?” Just like that, totally natural and possibly the start of a fabulous friendship.

The art of getting asked out

After college, I moved back to my hometown of Portland, Oregon and started all over again on the friendship front – and accidentally mastered the art of the random ask-out.

I googled volunteer groups to join and started going to networking events, using my honed conversation skills to meet people left and right. And the more I put myself out there, the better I got at it.

Then one evening at a fundraiser, I found myself talking to a cute guy about our study abroad experiences. I was genuinely curious about his time in Spain, and the possibility of making another new friend. So when he ended our conversation with “Would you like to grab dinner with me sometime?” I was completely shocked.

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It was then I realized that the exact same skills of making friends applied to getting asked out on a date. The difference was simply a little more courage (or in that case, pure naivety). I’d become so comfortable making small talk and meeting new people that I’d started letting my personality shine through and discovered it was actually pretty flirtatious. And men were starting to pick up on it – literally!

I started getting asked out in the most random places: at the bus stop, on an airplane, in the Nordstrom shoe department. The more people I met and meaningful interactions I initiated, the easier and more fun the next ones were. Having fun with it made me want to practice more and more, which is only natural when we find something we enjoy doing.

From conversation skills to OFFline dating coach

A few years later, I made the move from Portland to Chicago for a change of pace, and used the same skills I’d been honing for years to meet new people and flirt my way around the city. One day, some girlfriends pulled me aside and asked how I was able to “do it”.

For the first time ever, I thought about what I might be doing to make strangers feel comfortable talking to me – and how I’d been able to overcome those awkward days in middle school to get to this point.

I came up with a short list of natural conversation starters and everyday meeting places, then presented it to my friends. They loved it, and the first iteration of my OFFLine dating workshop ‘How to Attract with Allure + Approachability’ was born.

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So what’s the secret to confidently striking up a random conversation, no matter your current social comfort level? Practice, practice, practice – and a small dash of bravery.

Start with talking to people just outside your comfort zone and work your way toward those you’re attracted to. It really is the same conversation skill set.

Share a story, ask a question, or give a compliment and make it genuine. Don’t worry about the outcome, just enjoy the moment for what it is and see where the conversation naturally goes.

The more you do it and push slightly past your comfort zone, the better you’ll get and more fun you’ll have – which only makes you want to repeat the process over and over again.

Who knows, someday you may find yourself being asked for your expertise in how to meet people!

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