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How Do You Make Conversation with Strangers?

By: Jen Shoop

At a recent event, I was introduced to a lovely woman who, within the first few minutes of conversation, left me feeling deeply at ease. By the end of the night, I felt we were old friends; it seemed impossible we’d just met a few hours earlier. I was reflecting on her generous energy and it occurred to me that one thing she’d done to quickly establish our intimacy was repeat my name multiple times within the first twenty minutes of getting to know one another: “Jen, it’s so good to meet you–” and “Jen, where do you live?” and “I was just telling Jen that…” I’ve heard that repeating someone’s name as soon as you learn it is a helpful mnemonic, but I’d not considered the way this repetition can make the other party feel seen, recognized, invited. Somehow, hearing my own name signaled that this woman was actively listening to and engaging with me on a meaningful level. I am determined to follow suit the next time I’m at a cocktail party. I want to model this woman’s present-mindedness during that opening “how do you do” exchange!

I’m curious – what are your best strategies for making conversations with strangers? Do you have go-to questions? Do you try to look up the guests who might be there in advance?

A few tips and reminders I’ve picked up over the years (several from Magpie readers) when navigating new social scenes:

+Reframe the entire event as an opportunity to show up for other people. Dwell less on yourself and more on those around you.

+Everyone feels awkward making new friends — it’s not just you!

+Ask a lot of questions.

+It’s always much easier to be approached than it is to approach. Be the brave one and introduce yourself.

+Mind your body language — crossing your arms or angling yourself away from the crowd can make you seem less easy to approach. (I also remind myself to put a smile on my face when entering a room!).

+It’s natural to gravitate towards people you know, but keep an eye out for loners. We’ve all been the wallflower before; offer that person a kindness. It’s like giving your past self some good karma!

+If you don’t know how to respond to a strange, rude, or unsettling inquiry, buy yourself time by saying, “let me think about that.”

Please share for those of us deep in the thicket of new parent events, soccer sidelines with strangers, and the like!

Post-Scripts.

+On female friendships and the things that matter.

+How do you balance your friendships?

+The velvet underground. (A musing on identity and past versions of ourselves inspired by Stevie Nicks.)

Shopping Break.

+I want this sweater tee in all the colors! Perfect way to balance out fuller skirts, wide-leg trousers, and barrel-leg jeans!

+Another great basic for the incoming season: these turtlenecks. They are super fitted and a gorgeous, polished material. They also released their iconic turtleneck in a DRESS form this fall and it’s nearly sold out. (Use code MAGPIE15)

+Colorful to-go coffee cups for your next fall gathering.

+Obsessed with this brown silk top. Meanwhile: husband shirts in a fab new fall pattern! These are made of an ultra-soft, airy cotton; you can tuck them into jeans! (Use code JEN-15)

+OMG Me+Em is killing it this season…! THIS COAT! Vibe for less with this. But back to Me+Em: I meannnn, their fall dress curation…! This cord dress, this tweed one, this floral, and this crochet collar?! Swoon!

+Elevated fall lounge set for under $50. Pair with fall sneaks!

+Gap fall denim goodness: this jacket, this skirt, and this cropped denim overshirt (very similar to one I have from a few seasons back from La Ligne that I love to wear over fall dresses as a kind of jacket!). Both of the Gap colors are fabulous.

+How I’d style the denim overshirt:

GAP SHIRT // DOEN DRESS // TB BAG // ISABEL MARANT BOOT // JENNIFER BEHR EARRINGS

+Love the knot button detail on this Tuckernuck cardi.

+La Ligne released their cult-favorite Colby in a sweatpant material! (Code: MAGPIE10)

+Alice Walk restocked their best-selling cashmere wraps in lots of great colors!

+Gentle shampoo for highlighted hair. More European pharmacy favorites here.

+Perfect waterproof clogs for walking the dog this fall. For something a little splurgier, I still pull out my handy no. 6 boots every fall/winter. They are lined in shearling! The best. Go up a size to accommodate winter socks.

+Obsessed with these entryway hooks.

+I’ve been noticing some collar embellishments this fall — it started with this $$$ Prada and now I am eyeing this and this!

This post may contain affiliate links. If you make a purchase through the links above, I may receive compensation.

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