Conversation Starters for the Socially Challenged Part 2

two women and man talking
Photo by cottonbro on

Back in 2011, I wrote a post where I offered some conversation starters for those who find it challenging to strike up a conversation with new people–especially in the context of a party or other social gathering.

With the holiday season in full swing, I thought it would be a great time to revisit some of these scenarios and provide some new conversation starters for those of you who find it challenging to mingle with strangers (potential new friends) at holiday parties or mingle with humans in general. Consider this my holiday gift to you!

Scenario #1: You’re attending an obligatory holiday party that you don’t want to attend 

[Disclaimer: You’re actually not obligated to do anything you don’t want to, but that is for a whole different blog post–or something to address with your therapist.]

Before the party starts, you have some pre-work to do. First, think of one positive aspect about attending this party. It could be the open bar, the opportunity to network and generate leads for your new side business, the ability to gain a new friend, the chance to laugh at Karen’s kitschy holiday attire, or maybe Santa Claus will be there pouring whiskey shots for everyone

Second, arm yourself with possible topics of conversation. Remember, you don’t have to fall victim to boring conversations–you’re in the pilot’s seat. Some possible topics of conversation include: 

  • a favorite sports team, preferably one who is doing surprisingly well
  • Your fresh take on a topical news story
  • the rise and fall of the American mall 
  • How tap dancing is a dying art in desperate need of a comeback 
  • Your favorite DIY strategy for home repair
This is what happens when you don’t use conversation starters! You get stuck in awkward interactions with no exit!

Once you arrive at the party, familiarize yourself with the layout and identify strategic locations where you might want to stand or move between throughout the party. Locate the nearest exits, bathrooms, people you’d like to avoid at all costs, and the open bar. Throughout the evening, rotate between these strategic locations so that you’re not spending too much time in one place and therefore stuck talking to someone whom you despise.

Remember to incorporate the key strategies of having a conversation: identify yourself and your relation to this party. Ask for the other person’s name and for them to identify their relation to this party and then say nice to meet you. If you can’t find common ground from that initial interaction, use one of your pre-planned conversation topics to keep the discussion going! Once you’ve reached your limit, excuse yourself to one of your strategic locations.

Now you’re ready to mingle and dare I say have a good time! 

  • Here’s what this might look like:

(At home, before party)

Thinks about one positive aspect: the open bar filled with top shelf liquor. Equips self with two possible conversation starters: the new Green Bay Packers coach is having a record-breaking season and the rise and fall of the American mall. 

(Enters party)

Looks around the room and notes the location of the stairwell, exits, bathroom, and most importantly the open bar with top shelf liquor. Spots Garrett, the annoying neighbor who doesn’t mow his lawn in a timely fashion, mentally adds him to the no-interactions-at-any-cost list. Sees someone who looks remotely interesting, cautiously approaches.

You: Hi, I’m [insert name]. I’m [name your relation to the person affiliated with this party.] shakes hand, looks the other person in the eye.

Someone who is remotely interesting: Hi, I’m [insert name.] I’m [names relation to the person affiliated with this party].

You: This is some party. And top shelf liquor?!

Someone who is remotely interesting: It’s about par for the course.

You: I wanted to bring a gift for the gift exchange, but I couldn’t find any malls that are open anymore! I miss having one location where I can do all my shopping and have a snack or play a quick arcade game.  What a shame. 

Someone who is remotely interesting (eyes widen): I know just what you mean. I was just saying the other day that we’re a far cry from the glory days of the American mall. Why I used to spend every weekend walking the mall with my high school crew!

You: Exactly. Well, I’m going to sneak off to the restroom. Great talking to you, [insert their name]. (exits)

Scenario #2: A holiday party where you’re bringing a guest that knows no one

You’re not Karen’s baby-sitter, but it would be much appreciated if you helped Karen find her footing before you make a break for the bar and leave her to fend for herself with all of your friends & acquaintances. 

This one is fairly straightforward. Find someone in the crowd you has something in common with Karen, make the introduction and connection between the two, and make your exit!

You: [Your guest’s name], I’d like you to meet [name of person you’d like them to meet], my [insert relation to that person]. You both [insert what they have in common], so I think you’ll have a lot to discuss!  (waits for them to start talking and then scoots off to the open bar)

Scenario #3: Backing out last minute from a party you’ve committed to attending

Maybe you accepted the invitation prematurely and when the actual date rolls around, you’re no longer interested in attending. Happens to the best of us! It’s okay to change your mind and say no. Situations change and you might be too tired to attend a holiday party filled with laughter and good cheer. Or perhaps you are wrapped up in your favorite blanket on the couch and moving isn’t an option. Regardless of your reason, all you have to do is reach out to the party’s host directly and change your response. No need to make up some elaborate excuse or fake emergency or profusely apologize –be brief and direct.

[You] Hi, [insert name of party host.] Unfortunately, I can no longer attend tonight. Have a great time!

That was so easy, wasn’t it?! 

Challenge scenario: Cold call/text/email someone whom you haven’t spoken to in awhile to spread the holiday cheer

In the spirit of the holidays and new year, let’s challenge ourselves. True change and positive growth happen only when we push ourselves outside of our comfort zone. Think about someone whom you haven’t spoken to in awhile, but would love to catch up with. Contact them first! You don’t have to wait for them and I know they would love to hear from you. You can use this email/text template below:

Hi {insert their name],

[insert holiday greeting tailored to their they observe]. I’ve been thinking of you and I was remembering [insert a memory from a joyous moment you shared with this person and why it was special]. I hope you and your loved ones are doing well!

I’m [insert a one-sentence summary of something exciting that’s happening in your life]. I would love to hear from you some time!

Much love,

[Your name]

If you’ve made it this far, then you are quickly on your way to mastering the art of social interactions. I wish you much success in your holiday interactions and beyond, and I can’t wait to hear all about your renewed connections to your long lost friends! 

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