A Couple Standing Beside the Bicycle while Having Conversation

Break The Negative Cliche With Fun And Engaging Small Talk

Whether you like small talk or not, the benefits of a fun and engaging conversation can positively affect your overall social happiness. And yet it is still a skill that can create a few barriers when poorly done, especially on a first date! Let’s look at how to be witty and intelligent but also engaging and attentive.

Drawing a Mind-Numbing Blank

Cassy glanced at Emily as she stared off into space. They shared an office on the tenth floor, overlooking the Hudson, and both have had their fair share of admiring the view and taking a small mental break during their hectic work weeks. Marketing was a competitive and stressful occupation, yet they have found a winning combination. Working together, they complemented each other’s strengths and covered each other’s weaknesses.

They had a deadline due tomorrow, but Emily had not been focused, her gaze perpetually locked on the river. She seemed to be analyzing something mentally.

“Earth to Em,” Cassy said, smiling gently as Emily glanced at her. “Everything O.K?”

“What? Yes, everything is fine… I just…” Emily shrugged before blurting out, “I can’t believe I said that; that’s all.”

“Said what?” Cassy asked in bafflement, “You have not spoken a word today.”

“No, not to you… To my date last night…”

“You went on a date? You never date!” Cassy exclaimed excitedly. 

“Tell me everything!” she gushed, workload forgotten as she shifted to get comfortable in her chair.

“There is a reason I don’t date…” Emily began.

“Oh, come on! It can’t be that bad!” Cassy laughed. “What did you do? Blurt out that he was handsome while you wanted to seem cool and collected?”

“No… that was definitely not it… I… Well…”

“Ah, man,” Cassy said, her expression falling into a look of anticipated horror, “You didn’t tell him you loved him on a first date… Did you?”

‘What! No! Why would I… Never mind.” she said, shaking her head.

“No, he was talking about his family and how he loved his little half-brother, who was staying with him. I sensed that he was losing interest and talking about anything to distract himself. He had talked about how he loved a witty conversationalist just minutes before, and I tried to make a joke, but it backfired…”

“What does his half-brother have to do with that?” Cassy asked, thoroughly confused.

Emily’s expression flattened as she stared at Cassy.

“Sorry, please continue,” Cassy said, slightly abashed.

Snorting before grinning at her friend, Emily continued. 

“I tried to make a joke… So I asked him which half of the brother he has, just the legs or the torso…” Emily finished, grimacing as she did so.

Cassy put her hand over her mouth, eyes wide before chuckling softly. 

“O.K., I’ll admit that it is not as bad as telling someone you love them on a first date, but damn…” Cassy grimaced.

“I had no idea you were so bad at small talk. You are normally fine during meetings and around the office.”

“That’s because I am not trying to date someone at the office!” Emily exclaimed, utterly dejected.

“Don’t worry; it’s fixable!” Cassy rushed to assure her.

“Well, perhaps not with this particular date,” She amended at Emily’s dubious look, “But I can help you prepare for the next one.”

The Solution to Your Chit-Chat Problem

First of all, I suggest you relax. You are putting too much stock into having the perfect first date, which is messing with your confidence. If you keep stressing about it beforehand, chances are that you will be more likely to be on your guard on the date. And it would not be spontaneous.”

“So what would you suggest? How do I stop stressing about it if I know how bad I am at it?” Emily asked in a small voice. 

“Well,” Cassy said, reassuringly squeezing Emily’s hand, “You are amazing at research when we need to do a marketing pitch.”

“So do the same before your date. If you met him on an app, make sure you know his interests and hobbies. See if you have anything in common and then read up about any of those points you find interesting or have common ground on.”

“But what if I don’t like anything he likes? Do I fake it and try to appear interested?”

“No! Never fake an interest. Sooner or later, it always catches up with you. You do not want the truth to come out on your seventh hike with the guy that you actually detest the fresh air and sunlight.” Cassy said sagely.

“Good point… I really don’t like hiking… But what if he is really hot?” Emily asked with a pleading glance.

Cassy laughed and shook her head. “Even then! Otherwise, you will waste both of your time, rather cut him loose and look for someone you can converse with.”

“You can also make sure you have a list of common questions you ask on a first date.” Cassy continued. “It does not have to be boring ‘What is your favorite color or favorite movie’ questions either.”

“Make sure that they add value, but also allow the other person to talk. Because while they are talking, it would be the golden opportunity for you to let your strength shine.”

“And what’s that?” Emily asked, looking up from her notebook in which she had been jotting down the points.

Shaking her head, Cassy sighed. “Sometimes I wonder how someone so smart could be so clueless…” she jokingly said.

“Your ability to be an engaging listener, of course! You always make people feel like they are the most important person when talking. It makes people feel special and really gives you the ability to ask intelligent questions.”

“Which leads me to my next point. Please stop trying to give him the answers you think he might hear. Contrary to what some people will tell you, men want to know that you are interested in them, not just giving the same generic, cookie-cutter answer that all women think they should give.”

“Right… Of course… Like what?” Emily said, pushing her lips and leaning in attentively.

Cassy snorted again. “Wow, you really are clueless,” she jokingly said. 

‘Well, for starters, don’t tell him you think he is funny if you don’t really think he is. Or excessively laugh to make him think that you find him hilarious while it was only mildly amusing. Always be truthful in your reactions and in what you say.”

“And above all else, just be yourself. Get to know the person while having fun, and if you are not feeling the connection, make a graceful exit, like saying that you have an early morning or another engagement.”

Conclusion

While small talk comes naturally to some, it might be a scary prospect to others. Keep a simple formula in mind; it will remove the pressure to seem polished at the skill. Being engaging, attentive, and in tune with the person you are talking to can open the possibilities too much more. Remember to be yourself and have fun! 

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