3 Conversation Tips For When You’re At The Next Holiday Party

Dress: Nordstrom in-store, but gah – was not able to find it online! However, here are some emerald dress options that would be so pretty for a holiday party: ASTR The Label Lace Midi Dress (Comes in a ton of cute colors and is very flattering on!) + Reformation Piper Dress + Eliza J Fit & Flare Sweater Dress. If you are open to colors outside of emerald, here are some additional lovely options: Halogen Bow Back Shift + Topshop Plain Satin Slipdress + Reformation Alma Dress (LOVE the leopard print!) | Hat: Wool blush beret. Similar here + here.| Purse: Natasha Glitter Clutch. How fun is this purse?! It also comes in gold and blue!| Necklaces: Layered the Lydia Statement necklace with the Micaela Erlanger choker necklace. Love this necklace as a layering option, too! | Shoes: Everlane mules. The ones shown are past season and no longer available, however the Editor Slingback flats are similar!

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Ah, holiday parties.

Do you love ’em or hate ’em?

Personally, they’re some of my favorites of the year. I always love catching up with people who I’ve missed dearly. Close friends, of course, but I also usually end up talking with people who I haven’t seen in a long time, or even meeting new friends. It’s what the season’s all about!

You know what I love most about holiday parties? When I strike up a conversation with someone and end up having the best time. The ones where I laugh, have heart-to-hearts, and oftentimes even learn something. The ones where it feels like I could keep talking for hours.

….But, sometimes, the total opposite happens. Two minutes in, we’re done talking about the weather, and are grasping for straws. You know what I’m talking about, right? The “smile and stare around the room because we both don’t know what to say” situation. Those conversations are the worst, aren’t they?! I usually end up feeling suuuper uncomfortable, then nervously blabbering on and on about something that doesn’t make much sense. #Awkward

At the end of an evening, Doug and I love to regroup by asking one another, “Who was your favorite person to talk to tonight?” and “What was the most interesting conversation you had?” (They’re often correlated!) We each usually will have one or two conversations that really stick out from the night because they flowed so well.

What is it about those conversations that just *work?*

We’ve quite literally asked that question to one another. We’ve analyzed. We’re like Sherlock Holmes and Dr. Watson, only BETTER. (Okay, maybe not better. But we’re both pretty observant people and we’re non-fiction so…two points for us.)

Turns out, we’ve found some commonalities behind the conversations with which we jive well. After years of doing the after-party analyzation, we’ve come up with 3 key things that we both now try to keep in mind when chatting with others.

I swear by these tips. They work. And I’m excited to share our 3 conversation tips with you, in hopes that they may help you as a bag of tricks if you’re finding that you need a little help in future!

Here they are!

Conversation Tip #1: Ask Questions

This is the biggest and most important quality of a great conversationalist. They, quite simply, ask questions.

How is the other person doing? What are their plans for the holiday season? Any travel plans for the year? Where did they go this past year?

This seems obvious, but it’s surprisingly easy to forget to do. I’ve been there; the scenario where I hug, say hi, and then I kind of…blank. (If you struggle with this, it may help to even make a list of questions before you go to the party in preparation!) A key thing that has helped me is to keep the words “Be curious” at the top of mind. Being genuinely interested in the person’s life is a flattering thing for that person — don’t be afraid to ask them about what’s new, how they’re feeling, and their thoughts/opinions on topics. You may even learn something!

One important note is to ask questions back if one has already been asked to you. It’s not only cordial to do in conversation, but it’s important for the flow. It shouldn’t always be one person doing the asking, or that person may begin to feel a bit of wear out.

Conversation Tip #2: Phrase Questions Openly

“Isn’t it a pretty night tonight?” sets up the conversation much differently than, “What did you do prior to the party tonight?”

Can you spot the difference? The first has a higher potential to set up the answer to be a quick yes or no (thus potentially stalling the conversation flow), while the second opens things up a bit more. The other great thing about the second is that it allows for multiple topics to be approached based off the answer. Did they go shopping at a holiday market? Perhaps you’ve been wanting to go and ask what their top recos are to do there. Did they see a new movie that just came out? Perhaps you’ve seen it too and can compare thoughts.

A careful phrasing of questions can really help to open up the conversation and its topics more. Here are some additional examples, to help demonstrate! Note the bolded phrasing — starting questions with these can really help to make your questions more open.

“Tell me about the trip to Italy that you recently took!”  vs. “How was Italy?”

“I thought of you the other day when I heard about the Shinola hotel opening up. What are your top recos to do downtown?” vs. “Do you like going downtown?”

“I know you recently started a new job. What have been the biggest adjustments with it? Tell me about how it’s going!” vs. “Do you like your new job?”

Conversation Tip #3: Have A Few Stories On Standby

Storytellers are some of my favorite people to talk to. After all, who doesn’t love a great story?! This can be anything from an interesting news story, to something personal that recently happened, or even a memory from the past.

I have the worst long term memory so I can’t offer up suggestions for pulling out the perfect memory from my dusty vault, but what I can offer up is that I’ll often go into a party thinking of a few interesting stories from the news, and I’ll also be prepared with stories regarding common questions that may pop up such as, “Do you like living in your new house?”

For example, using the question noted above, I was recently at a party and was asked how the transition to our new home has been. I said great, of course, but then I also told a story about how Doug and I were so nervous for the first night of sleep, because we thoughts our girls would have trouble alone in new their rooms after being in my mom’s basement with us for 4 months. We were shocked when they both basically put themselves to bed and slept 12 hours, which to us demonstrated that they were just so happy to be in their own rooms.

I always find that little stories help to highlight a point or answer best. And I love to listen to others when they provide the same, because it helps me to understand their point of view better!

One note here is that I do think it’s important to save long stories for camp fires or more intimate settings. A conversation is two ways, and if you’re the only one doing all the talking, it doesn’t let others have the chance to participate. If you find yourself getting glazy-eyes or fidgeting in return, you may have been talking for too long. That’s your cue to wrap it up and revert to conversation tip #1.  Of course, another great way to go is to – literally – dress the part. A fabulous outfit is always a conversation starter, I’ve found! Here, I’m wearing an emerald dress (similar here or here) combined with a blush beret, glitter clutch, and layered Lydia Statement necklace with the Micaela Erlanger choker necklace. I love pairing jewel tones together, especially during this time of year! They’re a fun and sometimes unexpected combination that looks both festive and chic.

:: Shop Outfit + Adorable Holiday Dress Picks Below ::

What are some conversation tips that you’ve learned throughout the years? I’d love to hear your thoughts and suggestions in the comments below!