Amazing Conversation Starters for Those Awkward Moments

First date

Haven't won any Best Conversationalist of The Year awards lately? You're not alone. We all hit that bedrock. There's the dreaded pause when even rock star schmoozers internally scream "Eeks, what now?" Don't sweat it, even if you're inadvertently sweating. In fact, if you are sweating, you could talk about that. If you're brave enough.

1. Talk About Numero Uno

And Numero Uno, of course, is you. Talk about yourself, especially if you've got a skittish, social turtle on your hands. Modeling how to open up gives her permission to come out of her shell. Just tell her whatever is on your mind (if it's appropriate...), or what you were thinking or feeling in the car on the way over. Was it the traffic? That you're self-conscious about meeting new people? Yeah, even acknowledging the awkwardness is fair game. You're defining yourself as approachable.

2. Weather or Not It's Lame...

Young woman underneath rainbow

Weather is the Switzerland of topics. It's neutral, familiar, non-controversial territory. Unless you're having a heated discussion about global warming (no pun intended) or chewing someone out for always turning the thermostat too low. But if weather is too commonplace for you, that's fine. Just look around. Make an observation about the atmosphere or people or decor. Then ask your conversation buddy for her opinions and thoughts.

3. The Serious Question Fake-Out

Even the least funny bone in the elbow can crack a joke. Act serious and earnest and say, "I have a burning question..." then hit her with a silly, random open-ended question like: "Which Disney character would you want to meet in person and why?" Or, "If you could travel to any place and time, where and when would you go?" There are countless "earnest" questions you can ask. It's a magical cure for silence. The awkwardness may live on, however. Oh well.

4. Complement the Ego with Compliments

Everyone needs a little shot in the arm now and then. Why not inject some genuine flattery into the discomfort? Surely something about your (maybe) new friend is praiseworthy: clothing, handbag, hair or one of their features. To keep the flow, ask where she got her apparel or hair done. Or describe what her eyes remind you of or how she makes you feel. If it peters out from there, you can talk about your own horrible or wonderful hairstylist, or how shopping at the 99 cents store isn't working for your wardrobe.

5. Non-Electric Current Events

Businesspeople talking

This may shock you, but certain current topics are supercharged. Time to unplug them from the discussion outlet and switch to the heartwarming human interest story you just caught on Facebook, juicy celebrity gossip, or events in faraway places. If you're not a news buff, own up to it. Admit that you aren't up on the things, and ask if your new partner in conversation crime knows the latest. And if she doesn't keep abreast of the news, ask why. She might have a story about that.

6. Next Stop: Education Station

Going through school was probably a drag, but reminiscing about it can be hilarious and fascinating. Elicit memories and stories with open-ended questions, along with the obvious "Where did you go to school?" It doesn't matter if it was high school or college, you can ask any number of questions:

  • What was the crazy team mascot?
  • The school fight song?
  • Any shenanigans or pranks to laugh about?
  • A favorite subject? Why?
  • Memories of favorite teachers or professors?

These are all irons on the gabfest-fire.

7. Connect Your Dots

Connecting Circles

No matter the occasion - party, business event or date - it works. Talk about how you're connected with the person in front of you. If you met through a party host, ask how she met that person and get her to tell a story. If it's a coffee date with someone from the online dating world, take full advantage. Be a scout. Be prepared. Study social profiles and mention the highlights that you want to know more about. Curiosity may kill the kitty, but it revives a dead-dog discussion.

8. Oh, The Places...

Just look at the typical online dating profile... everyone loves travel. It's universal, but everyone has a unique history and experience with travel that you can ask about. Where has she been recently? Any place she's planning on going to? Bucket list destinations? Leverage it by asking about any adventures encountered on her journeys. Then squeeze in your own - if she can stop talking long enough.

9. Go Fishing for Favorites

Are you sensing that your awkward-moment partner recoils at personal questions? Pry into her inner world through a less direct route: fish for what topics she's hooked on. "See any good movies lately?" "Ever hear of the band that's playing the song in the background? Do you like it? What kind of music are you into?" Go through the line-up: TV shows, foods, drinks, and sports. Soon you'll uncover her secret passion.

10. Provoke Peacock Plumage

Male peacock

Don't know what the person you're trying to get to know does for a living or how she occupies her time? Ask. Then ask what it's like. What's her favorite aspect of her expertise? What does she do to accomplish her work? Now, knead this into the mix if you can: ask her for advice or opinions on a matter you've been wondering about that's related to her knowledge. It ups the happy for both of you when her colorful feathers spread. And you just might learn something.

11. Make Something Happen

When you totally and completely blank out, don't lose hope. Invite your fellow-blanker-outer on a walk, or ask if you can get her something like a drink. It's really a slick way to deflect. Shifting the focus to movement will distract from the obvious weirdness. What's more, activity buys time, and you might think of something to say in the process.

12. Everything's Relative

People can't not have strong feelings about family members. When you ask, hopefully you'll get the positive emotions. It's sort of a crapshoot, so your best bet is to aim at questions about the younger, more adorable members of her tribe. Does she have kids? If so, she'll probably start gushing. If not, nieces, nephews, and grandchildren will do. Once that river is running, all you have to do is "Ooo" and "Ahh" as cute information and images freely flow.

13. What's In a Name

Businesswomen Wearing Blank Notepaper on Foreheads

Here's a great trick. It's acceptable to not remember the name you just learned moments ago. Take the grand opportunity of the cessation of chatter to ask. "I'm so sorry, what was your name again?" If she's normal, she'll be happy to repeat it. Then you can ride the wave to comment on how strong or beautiful it is, make a reference to someone in your life with the same name, ask what it means, or if they were named after anything or anyone cool.

14. The Holiday "In"

Mentioning holidays is handy any time of year. Check it out: "What did you do for [insert the last holiday]?" "Got something special planned for [insert the next holiday]?" Voila, easy as pumpkin (or whatever type of) pie. In rare one-off instances, you'll come across that oddball who just doesn't celebrate holidays. What then? Ask around that. "Why don't you...?" It's a way to gather some 411 on her lifestyle, values and beliefs.

15. She's Got It Going On

Know what works for people you know and people you don't? Just a "what's going on in your life these days?" Wide open question, right there. There's no way to shut that question down, except by saying "nothing." If she really does say that, jovially ask, "What's it like to live in that vacuum, what is nothingness like?" Of course, regular people will have all kinds of things going on, challenges and triumphs, and stories will break open out of that.

When All Else Fails

If you're really dealing with a brick wall or your blood pressure is rising to the 43rd floor, gracefully make an exit with the genteel classic excuse, "It's been nice chatting, do you know where the restroom is?" It doesn't matter if you really have to go. Locking yourself in the stall and taking a deep breath before you return to the social scene probably won't hurt.

Amazing Conversation Starters for Those Awkward Moments