Am I Making This Awkward for You?

It's Monday. I'm here for you.

Jul 10, 2023

The Pick Me Up is a Monday morning newsletter filled with advice, personal stories, and tips to help you get out of bed and jumpstart your week.

Greetings, friend! It’s me, Jen Glantz.

Last Thursday, I took the day off of work and went to the spa.

I don’t remember the last time I did something like that. Hours after giving birth, I asked Adam to hand me my computer and I replied to non-urgent emails.

I’m addicted to work.

So much of my happiness comes from silly little goals I’ve set for myself that amount to non-stop anxiety and the desire to always be plugged in.

I crave feeling needed and what needs me more than my inbox, my to-do list, a marked-up grand plan that I have for myself in life?

For a while, when life was wobbly, believing that kept me buttoned-up and not so blue.

But now, the truth is, a whole crew of heartbeats need me to show up in all the best ways that I can for them and to do that, I need to have my sh*t together.

So after feeling a bit rickety and in need of a break from my routine, I took a ferry boat to a spa near Manhattan and floated around the pool all day with a friend.

Everything wasn’t cured when I got back home. My anxiety came with me to the spa and sat still in the locker room for the day. My to-do list snuggled up in bed with me that night. The love bugs I take care of looked at me like I’d been gone for days.

I don’t know when I’ll do something like that again for myself. But I do know this:

If you don’t give yourself a break, nobody else will.

In this issue: don’t forget to wear sunscreen and how to help awkward coffee dates when you can’t stop making them awkward.

Why you’re getting this: I'm Jen Glantz and this is The Pick-Me-Up newsletter. I've been sending it every Monday, for 8-years, to thousands of awesome humans, just like you. Thank you for letting this email live in in your inbox. It truly makes my heart explode with joy.

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📚: I bought this to flip through during the moments I need a pick-me-up

🎧: I tried out this playlist of songs because it’s titled comforting music that makes you feel positive. It was good background noise.

Also, I’m so freaking excited to listen to this podcast. It’s going viral for a reason.

🛍️: Rounding up the summer poolside items I adore.

Sunscreen, you can’t forget sunscreen! My picks include this one for body and this one for face.

I love a good pair of inexpensive sunglasses and picked up two pair from Amazon last week. Here’s how I looked for the right styles.

Picked up a bathing suit cover up that’s comfy and loose fitting.

I was invited to a pool party and thought this was a fun gift to bring to the party.

💬: So go ahead. Fall down. The world looks different from the ground. - Oprah

Let’s Not Make This Coffee Date Awkward, Okay?

I don’t like calling myself awkward because I’m not.

I’m clumsy, nervous, self-conscious, and so eager to make a stellar first-impression that going out for coffee with a brand new friend can be so anxiety-inducing that I take it out on my nail polish and scratch it all off beforehand.

I met an internet friend for coffee and it all felt so fizzy.

She was successful, cool, put together, and calm,

I had thick vertical deodorant stains all over my shirt and I had to do a quick baby feed before heading out so I forgot to run a comb through my hair. More than my appearance, my confidence was missing. I couldn’t think of one work win to share with her and feared she’d view me as, dare I say it, a washed-up flop.

I was so all over the place during our coffee chat and said all of the wrong things.

Nothing haunts you more than the things you wish you didn’t say and the things you wish you did.

Adam later asked me if it was that bad or if I was being dramatic.

I told him how I asked her the same question three times (I blame that on postpartum brain fog) and when she asked me what I was working on these days I simply said: a little bit of this, a little bit of that.

Friends, it was SO bad that 35-minutes in, she looked down at her phone, pretended to check her email and said: Sorry, love, I actually have to run.

I offered to walk her to the subway and she tossed her coffee, gave me a hug, and went off without me.

I replayed the coffee meetup a million times in my head and here’s what I think happened.

I was a mess from the start.

Here’s what I wish I did differently

Offer to buy the coffee but don’t cause a scene

I do this thing where the second we walk into the coffee shop I aggressively say: I’m buying your coffee today and if the other person pushes back, I rush up to the counter, pull out my credit card, and demand their coffee order.

While buying someone’s coffee is a nice gesture and it’s something I like to do, especially if they traveled to come meet me in my neighborhood, there’s a way of doing it that’s not awkward or forced.

I should have said something like:

Jamie, it’s seriously so good to see you and i’m grateful you traveled all the way here. Let me grab your coffee while you find us a table, okay?

Jaime, thank you for coming all this way. Coffee is on me today!

What are you thinking of ordering? By the way, I want to buy your coffee today as a thank you for helping me out with all the website stuff last month.

If they say: no you don’t have to do that! I think it’s a good idea to offer once more and if they push back again, let it go. Buy your own coffee and let that person buy their own too.

Settle down before you jump right in

I’m not a small-talking machine. After I force the other person to let me buy them coffee, I usually sit down with them and get to the point.

So tell me about the biggest mistake you made with your company?

What’s keeping you up at night?

What’s your number one regret.

I don’t ask those exact questions - but that’s sort of my vibe. I don’t like to waste time talking about the heat wave or how delicious oat milk is, I want to have a conversation as if we’re lifelong friends, and not people who met 30-seconds ago.

Instead, it’s nice to have 2-3 intro topics, that aren’t generic but aren’t ooey gooey either, to bring up before talking “shop” or getting vulnerable.

I saw you posted a few books you were reading this summer. I’m heading to the library later today, any reads you recommend I pick up?

I was thinking about how we got connected and realized we never talked about how we both worked at xy Communications at different times. What was it like when you worked there?

You seriously have the best style. Where are you shopping these days?

Come to the table with questions & answers

One praise I want to give myself is that I’m really good at coming to a coffee meetup with questions to ask the other person. Conversation is a back and forth dance. I like to have important and thoughtful questions to ask the other person.

To do this, I’ll spend time looking at what they’ve been up to lately or even ask them things like: What’s the last fun thing you worked on? What’s next on the list for you?

I prepare around 5 questions to ask the person so that when I arrive, the coffee chat has somewhat of an agenda and even when I get nervous, I have questions that help me guide the convo.

A socially skilled friend of mine said: know what the purpose of the coffee is before you go. If it’s to connect, keep the questions light. If it’s to become professional contacts, gear some questions to work. If it’s neutral, stay in the middle.

But it’s also important to come to the table with answers. I fumbled when the internet friend asked me what I’m working on. I had an answer but felt too icky to answer it so I just brushed off her question. That made continuing the convo hard.

Have answers to questions like: what’s new? what are you working on? what’s important to you right now? what’s next?

Ask for advice on something you really need advice on

That same socially skilled friend does this amazing job of flattering people by asking them for advice. She’s heading to Italy next month and asked a stylish friend of ours to eyeball her packing list and give feedback on different outfits.

It flattered that person and made them feel special, valued, and seen.

Before coffee chats, I want to start thinking of one thing I need advice on and ask the other person for help with that.

You’re so good with branding and I wanted to ask your advice on something. I want to change my newsletter name, which of these 5 options do you like best?

You’ve traveled to so many places. I want to plan a trip next year and am deciding between Greece and Italy, which one did you enjoy?

It’s been a week since that coffee chat and I’ve thought about the interaction for way too long. As the time has carried forward, it wasn’t as bad as I thought it was when I look back. If anything, it taught me that what I need to do is be more aware of who I am and come to the table with more intention.

Own up to the deodorant stains and explain what it means to be working on: a little bit of this, and a little bit of that.

The Monday Pick Me Up

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