A very good cup of coffee. Circa 2017

When I check my email in the morning, I hold my breath and cross my fingers, willing the powers at be to give me just one thing: An invitation out to coffee.

After 18 months of work-from-home life, I’m ready to get back out there again. To chit-chat and connect. To reintroduce small talk into my life. And I want you to join me. So come on, let’s meet up. Let’s network. Let’s find some synergies, bitch about nothing, build the thing. Yes, together, let’s change the world in 55 minutes over foam hearts and leaf art.

Please?

Meet me on the streets of New York City and let’s reminisce together about our favorite restaurants. Give me a reason to put on my favorite long dress and be embarrassed that I haven’t painted my toenails all summer. Make me wonder what train to take and maybe even force me to quickly look up your email address from my calendar app and send you my ETA in a panic from the subway platform. Show up late, show up early, don’t even show up at all, I won’t care. You’ll have at the very least given purpose to my day, you’ve gotten me out of the house.

Yes, of course, we can do this all while staying perfectly responsible and COVID safe. I’ll wear a new mask on the subway, just for you. I’ll sanitize twice before we elbow bump. We don’t even have to go inside together — we can meet at one of those coffee stands in Madison Square Park and avoid the dog poop as we take laps together until we’re dizzy. We’ll never even have to make eye contact or cross-contaminate each other’s air. Look, if it makes you feel better I’ll even check your vaccination card before I take your latte order.

What do you say, shall we get something on the books?

If this all sounds good, let me text you my Calendly link and you can pick a time that works for you. Honestly it doesn’t even have to be a time that works for me. Just tell me anytime and I’ll be there. I’ll even account for the fact that you’ll probably cancel twice on me before it actually happens so I’ll block out my calendar for the next three weeks to play it safe.

You might wonder what we possibly need to talk about IRL that we couldn’t do on Zoom. And to that, I’ll say, plenty of things. For instance, I can comment on your shoes. You can tell me how you weren’t prepared for rain today. We can form an instant bond at our mutual annoyance that the cafe ran out of simple syrup.

And because I know in-person conversations might give you a little bit more anxiety and social pressure than usual, I’ve helped you out by writing out a brief conversation script to take the edge off of those awkward first five minutes. Here it is:

1. Say hello; express extreme excitement to see me.

2. Tell me all about your last IRL business interaction, the last time you commuted, or some crazy thing you saw on the way here.

3. Tell me again how weird it is to be doing anything in person.

4. Ask me a series of rapidfire questions to recalibrate how you know me and jog your memory about the things important to me in my life. If you want to get fancy about it, the trick would be to ask in a way that doesn’t make it obvious you’ve forgotten these things. But even if you did forget, I’ll forgive you. Example include:

• Where I live: “Where have you been living all of this time? Did you stay local?”

• Where I work: “How’s job stuff going?” (The key is to play it safe. Stay vague if you don’t know.)

• If I have kids: “And the family? Anything new?”

• If I got COVID: “I hope you’ve stayed healthy throughout it all…”

Round out the last five minutes or any unnatural pauses in conversation with this catch-all phrase: “Ugh, everything is just so weird right now.”
 (Note: Max of 4 uses in a 60-minute coffee date.)

You don’t even need to memorize this. In fact, you can just keep looking down at your phone the whole time we’re talking and follow along. I won’t mind, I’ll be too busy wondering if the guy on the street carrying three FreshDirect bags full of cat food is about to throw his shoe at us.

What’s your schedule like next week? Shall we pencil something in?

I’m not even asking for pen. I’m super flexible. I’m only asking that — on the off-chance that you do decide to go into the office — you put me right at the top of your shortlist of people to call.

I know it may seem like I’m sending you mixed messages. I know two years ago I asked you please, for the love of java, stop inviting me out for coffee. But those were simpler times. I was ignorant back then, didn’t know how good I had it, what with my 1,200+ coffee-related emails and triple-decker-stacked afternoons of back-to-back meetings. Compare that to today, when my heart skips a beat just seeing a promotional email from Starbucks.

I’m not too proud to admit this: I still haven’t figured out my perfect French press pour. I’m jittery in the mornings and catatonic in the afternoons. So let’s just call things what we are and leave the caffeine stuff to the experts.

Tell me what you need, and I’ll be there. Are you trying to get a job in VC? Or maybe you’re looking for some fundraising advice? Do you only want to meet with me on the off-chance that I’ll like you enough to introduce you to someone you really want to know? I can work with that. Or maybe it’s career advice you’re after. Let’s meet up so I can download your brain then refer you to one of approximately 50 different blog posts I’ve written on the topic. When’s the last time you negotiated your salary, how can I help? Are thinking about executive coaching and need a few referrals? Looking for an all star designer for your team? Help me help you by putting my rolodex to work. Remind me what it’s like to be needed.

Do you think this all sounds a little crazy? Desperate, even? Well maybe like we should meet up and talk about it.

How’s Thursday at 3?

Originally published at Dry Erase.