Jay Baer says there's a lot at stake. Finding the correct words might mean the company gets to keep you.

Washington - After booking her first JetBlue flight recently, Kathie Baker was stunned by the confirmation email.

“First dates can be a little awkward,” it declared. “But that seems impossible with someone like you. Just to be safe, let's start with the basics.”

The airline then proceeded to describe its in-flight amenities:

“Favourite colour: Blue”

“Favourite song: Leaving on a Jet Plane”

“Relationship status: Single & ready to show you 85+ amazing destinations.”

“It was creepy,” says Baker, a translator who lives in Pittsburgh. “Almost stalkerish.”

The missive is part of a series of welcome messages sent to new customers. And it isn't happening in a vacuum. Companies are struggling to find the right tone to take with their customers, particularly in the travel industry, which is having one of its most challenging summers in recent memory. The messages they send range from slick to robotic, and decoding them isn't difficult.

JetBlue wasn't finished emailing Baker. The airline next offered to send her special deals, adding, “We can skip the mushy stuff and start delivering great offers to your inbox ASAP.” Sample subject line: “We're all in! Are you?”

Baker wanted the emails, which she said were “in poor taste,” to stop. I contacted JetBlue on her behalf. The next day, the airline fell silent. “With any luck, they have permanently ceased sending these emails to me,” Baker says.

Perhaps. JetBlue's confirmations are part of a series of marketing emails that all new passengers receive when they buy a ticket, and unless Baker opts out of future emailings, it is likely that she will see more like them.

“We went with the unique approach to drive engagement and understand customer preferences, while introducing customers to the brand,” says JetBlue spokesman Morgan Johnston. “As you've no doubt seen over the years, JetBlue has a long history of fresh, witty, fun, inclusive and occasionally tongue-in-cheek marketing.”

To be fair, some customers approve of the tone. Bilal Kaiser, who teaches digital marketing in Los Angeles, recently received a JetBlue email with the subject line: “Fares from $59 - we literally couldn't fare less!”

“Hilarious,” he says. “Made me open the email even though I wasn't planning to travel anywhere at that moment.”

That's a sentiment Jean Tang, owner of a New York copywriting agency, seconds. JetBlue's irreverent dispatches “leverage a familiar construct, create instant intimacy, and they're funny as heck,” she says. “And they're well written.”

But this summer, is witty prose enough? This hasn't been an easy travel season. Lines are long. Prices are high. Tempers are flaring. Is an informal love letter from a travel company going to make everything right?

Jay Baer says there's a lot at stake. Finding the correct words might mean the company gets to keep you. In his latest book, “Hug Your Haters,” he found that simply answering a complaint was enough to keep seven in 10 customers.

“After all, no answer is an answer,” he says. “It's an answer that says, 'We don't care about you as a customer at all.' “

Instead of trying to cozy up to a customer and potentially making some of them feel uncomfortable, most successful companies deliver more standard and predictable responses to any troubles that may arise, says Marilyn Suttle, co-author of “Taming Gladys! The Busy Leader's Guide to Creating Fierce Customer Loyalty.”

Rather than saying, “I'm sorry if you were upset,” which only aggravates the passenger because it's obvious they're already upset, it's better to say, “I'm so sorry you were unhappy with your experience,” she says.

Experts say that the correct, and prompt, mix can make the difference between the right words and ones that fall flat.

“Sincerity is crucial,” says Taylor Davis, a manager at Litmus, an email analytics firm based in Cambridge, Massachusetts. “Especially if you're apologising. You never want your customers to feel like they are talking to a robot. A simple way for customer service teams to remain sincere is by adding a human element and style when communicating with customers. They should feel like they're having a comfortable conversation.”

The line between comfortable and overly casual is easy to cross. Consider Spirit Airlines' promotional emails, which have been heavily criticised for a lighthearted tone laced with sexual innuendo. For example, during the sexting scandal of then-Rep. Anthony Weiner, D-N.Y., in 2011, the airline infamously launched a “Weiner Sale” with fares - direct quote here - “too hard to resist.” Some of its other promotions are so risque they can't even be described euphemistically without offending readers of this publication.

Double entendres aren't limited to airlines. The Modern Honolulu hotel's award-winning “Friends With Benefits” guest loyalty program, for instance, provocatively invites guests to come back by saying, “We've always got room in our beds for another friend.”

Here's the problem: Although promotional pitches may be amusing or suggestive, the travel companies' side of individual email conversations with customers usually is of the cut-and-paste style, delivered mechanically and dispassionately. When a company initiates a conversation - as it did with Baker, the JetBlue customer - it's amusing and engaging. When you start the conversation, not so much.

And, of course, words aren't always enough. If something has gone wrong, nothing says “I'm sorry” like a refund or a ticket credit.

This summer, travellers' expectations aren't that high. They want a relatively problem-free experience, don't want to spend too long waiting in line and - if possible - they'd like their luggage to travel with them. They'd prefer not to pay too many fees and not to get service with a snarl.

It would be a good start for travel companies to devote even half the time they do working up their unsolicited email messages on answering customers with empathy and humanity.

* Elliott is a consumer advocate, journalist and co-founder of the advocacy group Travelers United. Email him at [email protected]