Return to site

How I Went From Socially Awkward Teenager To Dating Coach

Learn the secrets behind the three key stages of great conversation skills

The following is a continuation from the previous post titled, "How I Became A Socially Awkward Teenager"

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.

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.

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!

Camille Virginia is an OFFline Dating Coach, giving single women who are burned out with online dating, tips to find their match in the real world! Get your FREE copy of "Four Ways to Get Him to Approach You" at

All Posts

Almost done…

We just sent you an email. Please click the link in the email to confirm your subscription!

OKSubscriptions powered by Strikingly