The closest people in my life these days are people I met on the internet.
Sounds creepy, doesn’t it? It’s not. I met my boyfriend on a dating app called Hinge, my roommate of 6 years on a social media app called Facebook, and my boss, who I work for a handful of times a month teaching classes for his company, by sending him an email.
I met all of those people, and many of the other people I love dearly in NYC, by reaching out. By saying, “Ah, what the heck. What do I have to lose? I’ll reach out with a message, a hello, a plea to meet me in person cause I am exactly what they are looking for (I didn’t use exactly those words to my BF on the dating app – though I wish I did).
This hasn’t always worked in my favor.
I’ve sent hundreds of emails and social media messages to people I’ve never heard back from. I’ve asked so many people if they’d mind answering a question or two, grabbing coffee, or just being internet friends with me, and they’ve used silence to decline.
But one time I did it, and it paid off. It paid off majorly.
In February 2013, before I wrote my first book, I decided to binge read as many books as I could steal from the library. By steal, I mean I checked them out under someone else’s name, because my library card was frozen for MANY unpaid fines.
One of those books was written by an author I had never heard of before. I read the book, while sinking into the cushions of my couch, on a Friday night, when the snow was falling so hard that I felt like I was reading inside of a snow globe.
After I finished, I tweeted the author. I don’t remember what I said but It was probably emotional, poetic, and typed with frozen fingers.
The author responded – via email – unexpectedly:
Somehow, I pulled myself together, brushed the chocolate chip cookie crumbs off my PJ’s and responded:
One simple tweet turned into an email chain which turned into us meeting in person (which you can read here) and that one meeting turned us into good friends, who have grown closer over the years:
Reaching out is something I’ve stopped doing. It’s something I need to do more of.
It’s something I asked for advice on from the expert, my friend Molly, who I met four years ago over email, when one of us reached out to another, then we met for Sushi, and since then, have become good friends. Not only that, but she’s connected me to a group of amazing NYC girlfriends who have become my local support system.
Molly recently wrote a book called, Reach Out. I read it in one night and it pumped me up enough to have a game plan where I’m going to reach out to 5 people every week.
Check out my interview with Molly below:
JEN: We met because of a RO email (phew, thank god). After we chatted via email and then met for the first time for sushi, I had a serious girl crush on you and wanted to hang out again! So my question is what are the signs that someone wants to stay in touch with you after you’ve gotten together and you’re eager to connect with them again?
MOLLY: There are two main signs that the person wants to stay in touch with you and get together again: one, they quickly provide any follow-ups that came out of the meeting and two, they put you in contact with other people in their circle.
In our case, I went back to our emails after our sushi date four years ago (!) and I saw that right after we got together, you sent me a link to your good reads account. We must have chatted about books (actually we probably definitely did, knowing us) and you sending that follow-up so quickly was a sign to me that you wanted to stay in touch. Digging back into my inbox again, about a week after our sushi date I sent an email to my friend Bonnie asking if she knew you and saying I thought you two would hit it off. And now Bonnie is OUR dear friend! Me introducing you to someone else was also a sign to you that I wanted to stay in touch.
And of course the ultimate sign someone wants to get together in person again: they offer up some new dates they are free to get together again. But if they don’t directly ask to get together again but both of the above signs are there, 6-8 weeks later it’s perfectly fine to suggest another time for you two to get together.
Who would have thought that meeting at Nana Sushi over on Third Avenue four years ago would have led to such a great friendship between us?! You came to my wedding, for goodness’ sakes! I thank the stars for that RO email each day.
JEN: What’s your favorite email send off?
MOLLY: I like to end almost all my emails with “Looking forward to talking soon, Molly” or sometimes just “Talk soon!” It’s action-y without being too pushy. Of course, you can never go wrong with a classic, “Thanks!” either.
The only email signature I would skip entirely is “Kind regards.” It comes off as really spammy and impersonal – stay away!
JEN: What are you most excited about when it comes to people reading this book when it hits shelves in September?
MOLLY: Hearing from readers about the changes that happened in their life because of Reaching Out. As an author and blogger yourself, I know you know that there is nothing – truly nothing – that feel better than when someone tells you your advice or your stories or your words help them inch closer to their goals.
I like the idea that at the end of the day, life is just about helping each other inch closer to our goals. A partner helps you inch closer to your relationship goals. A trainer helps you inch closer to your fitness goals. And hopefully Reach Out can help you inch closer to your professional goal.
JEN: If you could RO any celeb, who would it be? What would you ask?
MOLLY: Hoda Kotb! I just love her. I saw her walking her dog once and it’s a year later and I’m still talking about it. When I can’t sleep at night I like to watch her and Kathie Lee’s fourth hour of the Today show videos on YouTube – they always make me smile. And I think this video of her accidently sharing her cell phone number on-air is a really great example of grace and humor and not sweating the small stuff when something goes unplanned.
The reason I haven’t RO’d to Hoda is because I don’t know what I would ask her! I am waiting until I have the exact perfect reason to email her, and then I will reach out. It has to be perfect though – only one shot for my girl!
JEN: If you’re on the other end of the RO and a person asked for either too much of an ask and you don’t have that time to give, what’s the best way to answer so that you don’t ignore their RO?
MOLLY: There’s a few things you can do here.
First, if you have zero time at all (it happens to all of us in specific seasons of life – don’t worry about it) I’d be upfront and tell them that that right now, you don’t have the bandwidth to do X but wish them them best of luck. It’s hard to be upset when someone is honest, responsive, and earnestly tells you they just don’t have the time.
If you do have a little time to spare, you could ask them to distill their ask down to one question you can answer via email or you could offer to introduce them to someone you know that might have more bandwidth to help them right now.
Additionally, if you are getting the same questions over and over again, you could write a Medium post or add a FAQ section on your blog answering that question and direct people to that. Another option is to offer a paid service – like allowing people to book your time for a half hour. You do this with Jen & Juice and it’s a great program! (Are you still running J&J’s? Maybe reword this sentence to how it makes sense and then link to it?)
Finally, if you are getting a lot of inbound requests for coffee dates and want to find a way to work them into your schedule, you could decide to work from a coffeehouse or your office’s cafeteria one morning a week, and schedule two half hour meetings at a time in the same location, and have people come to you.
PS. You can pre-order Molly’s book right here – it will inspire you to change all the important bits and pieces of your life – I promise you that!
