Finding ‘The One’—10 Ways Searching for Flights Is Like Dating


Searching for flights is exciting. In fact, it can make you feel downright giddy—especially if you think you’ve found ‘the one.’

But the process can also be time-consuming and a bit like a roller coaster. Often, it just doesn’t work out.

Endless love

Sounds like dating/falling in love, doesn’t it?

This realization came to me a few weeks ago when I was searching for Mr. Right–I mean, the Mr. Right of All Flights. I was hoping he—it, that is—would be Colombia (story at the end of the post).  I wasn’t asking for much, not a soulmate or a husband. Just a basic flight.

But it never came together.

The idea for this post, however, did and so, there was a silver lining. Check out my list of similarities/tips and perhaps your luck will be better than mine—in flight searches and/or dating.

1. The Online Process Is Similar

In online dating, you enter search criteria and click on profiles. Like the pic and the basic details? Click for more info.

Searching for a flight is similar. Enter the criteria. Hit the button. Flight descriptions come up—including date, time and price. Want additional info? Click again.

Tip: Enter the right search criteriaor you won’t get what you’re looking for. As you will soon see, a lot can go wrong.

Flight Search Results

2. Red Flags Appear and Should Be Taken Seriously

When dating, one often spots red flags. The man or woman you’re with gives  TMI or doesn’t share enough. Or has an outburst in a restaurant. Is mean to kids. Whatever.

Same thing with flight searches. The site acts wonky. Crashes for no reason. Withholds key information like taxes and fees. Or overwhelms you with too much.

Red flag-o-rama, you think. Fuggedabout it. I’ll keep looking, thank you very much.

Red flags

Tip: Pay attention to any/all red flags. If not, you’ll pay for it later.

3. Bait and SwitchMore Common Than You Think

He/she looks good. You’ve got things in common. A match, right?

Well, get to know them and surprise! They’re completely different. They’ve got the looks of a supermodel and the personality of an angry pit bull. Or  you’ve got a Jekyll and Hyde on your hands.

Halloween 004

It happens with flights, too. The price is sexy. You think it’ll meet all of your needs. You get psyched and press the ‘Choose this flight’ button.

Surprise! Now you see the flight’s  true colors. Fees and taxes. Multiple layovers, including 24 hours in Siberia (in the winter) or 18 hours, overnight in Detroit, arriving at 3 a.m.

Tip: Follow the advice found in Tip #1. By paying attention to red flags, you’ll avoid the bait and switch.

4. The ‘Good Ones’ Are Taken

If you’re single like I am, then you may have been told (or thought it yourself) that ‘the good ones are taken.’ You meet someone great only to discover they’re married.

The other folks you meet are OK, but not so wonderful, of course. You’re feel like you’ve arrived at the supermarket too late; only the crappy produce is left.

rotting study 2

Well, the same concept applies to flight searches. While on the United site recently, I kept finding great flights. Perfect ones. Mr. Rights in a sense.

Then, just as I’d click, it would say, “No more seats available.” Gone. Just like that. All that remained—flights with 3 connections.

Tip: Start searching early. Don’t wait until the last minute (although, in some cases, it does work out when looking for a flight.)

5. Who’s Paying for Dinner Isn’t Always Clear

There was a time when men paid for first dates. Now, it’s anyone’s guess re: what will happen when the check arrives.

Same problem with flights.

Sure, international flights are quite generous. They pay for all the meals and alcoholic beverages. There’s wine, too, which can make things romantic.

Domestic flights, unfortunately, are cheapskates. They typically just give you coffee and tea for free, maybe a ‘snack.’ Want a real drink or some food? Cough up some money.

Tip: Always have cash and a credit card or two on hand. On some flights, they’ll take one or the other, but not always both.

6. When You’re Not Looking, You Find ‘The One’

Right person, wrong time. Wrong person, right time. Great flight, too early. Perfect flight, price and time—but to a country that just had a nasty earthquake or is on the verge of a revolution.

One day, that dream flight pops up on on your computer—nonstop, a third of the usual price, leaving at the time of day you prefer and going to Tahiti. Sadly, you have to let it go. The timing is wrong. The reason? You’re going to be the best man at your best friend’s wedding (and he took a bullet for you were you were a teenager.)

Say goodbye to that flight. It’s ‘the one that got away.’

Tip: Pretend you’re not looking and maybe ‘the one’ will come to you. Or start early enough and allow more than enough time. Or, better yet, throw out the idea of ‘the one.’ There are many ideal flights out there, not just one.

7. Regional/Domestic Flights—Like Dating the Boy/Girl Next Door

Nice, familiar, easy…and yeah, kinda boring. Sure, I can easily score a good deal on a flight to Florida, but so what? It’d be like dating a guy friend with whom I’m platonic. The spark just isn’t there.

But find me a ticket to Indonesia and I get butterflies.

Tip: Keep an open mind. Although the international flights might look more exciting, you never know. You could fall for something more local, especially if the price and timing are right.

8. Beware of Beer Goggles

Drink too much in a bar and you might go home with someone you normally wouldn’t. Search for a flight while buzzed—and you might make the same mistake. Flight options that might not be appealing suddenly look great.

Be careful. You don’t want to wake up in the am., thinking—Oh god, what have I done?—now do you?

beer goggles

Tip: Search for a flight while sober. Simple as that. OK, one drink is allowed.

9. Priceline is for the Smug Marrieds–not Singletons or Commitment-Phobes

Remember the Smug Marrieds (from Bridget Jones’s Diary)? Well, I suspect they’re the ones who use Priceline. People who know how to commit. See, you name a price and then, if the site finds a ticket, you have to buy it. As in, you must buy it.

Um, I don’t know, but that sounds like premature commitment, and it scares the hell out of me. Maybe it’s too much commitment for people like me, aka, Singletons.

Am I commitment-phobic? Perhaps. I think I’d rather play the field a bit before committing.

Just Married, Dalat, Vietnam

10. Breaking Up—Not So Easy to Do

Let’s face it. Situations change. People grow apart. They separate. And breaking up sucks. One or both people get hurt. And if it’s a divorce, it could cost a fortune.

When you break up with an airline—cancel a flight, that is—it’s often painful, too. Want a quick annulment? Good luck. Whether you like it or not, you’ve made a pretty serious commitment. (Think Wild West Justice of the Peace with a shotgun under his desk.) Like a possessive lover, the airline won’t let you go so easily.

Now, if you have a pre-nup (ie, paid a ‘flex fair’ fee in advance), you might be able to get out of it or reschedule.

Tip: If you buying a very pricey flight, it might be worth going for the pre-nup.

My Dream Flight–and Why I’m Still Looking

OK, so back to my original story: my tale of flight search heartbreak.

Here’s what I wanted:

—Open jaws: Newark, NJ, to Cali and back from Santa Marta, both in Colombia.
—No BS or games–ie, crappy layovers or sleeping with–I mean, in–Bogota.
—A decent price via cashing in miles OR using a $300 credit I had. Meaning, the date—flight, that is—would be mostly paid for by United.

During my search, there were highs and lows, moments of giddiness and of thinking, “I’ve found ‘the one.” And the let-down of figuring out that I hadn’t.

I had, actually, but United wouldn’t let me use the $300 credit I had. I wasn’t happy and this, sadly, killed the romance. I walked away.

Actually, I’ve moved on…to Mexico and the Caribbean and other airlines.

Maybe I’ll get lucky with one of them.


Your Thoughts/Reactions/Experiences?

Have you experienced any of the above-mentioned similarities? If so, which ones? If you know of any others, please share.

Have you found ‘the one’? If so how many times? Which search engine do you typically use and why?

Any ‘bad (airline) breakup’ stories? Feel free to share. It might be therapeutic.

And if you’ve got search tips you’d like to contribute—for flight or partner searches—please share. You could be making an important difference for someone. :)

And if you think you’re my type, feel free to DM me over on Twitter. 😉

23 Responses to Finding ‘The One’—10 Ways Searching for Flights Is Like Dating
  1. Gray
    December 29, 2013 | 4:41 pm

    Oh, Lisa, I feel like I experience this every time I fly. It’s a very apt comparison.
    Gray recently posted..2013: The Year of Social Solo TravelMy Profile

    • CB Driver
      December 29, 2013 | 5:06 pm

      You, too, huh? LOL So I’m not the only one who’s still looking–he ha. :)

  2. Maria
    December 29, 2013 | 10:26 pm

    This should win a prize for the wittiest post of the year. I love the analogies you’re making here – so fitting.

    This is a post I will bookmark because I know I’m going to want to reread it often.

    #5 in the US this past year United and American only took credit/debit cards during my flights. No cash accepted.
    Maria recently posted..Haiku – Sustenance of LifeMy Profile

    • CB Driver
      December 30, 2013 | 8:45 am

      Thanks mucho, Maria–so glad you enjoyed it!! I wish there were such a contest. I’d submit it. :)

      #5, huh? They only took credit/debit? And they didn’t treat you to any small snacks? How unromantic. LOL

  3. Dyanne@TravelnLass
    December 30, 2013 | 2:41 am

    Most clever (and apt!) analogy, Lisa. Especially #6: “Right person, wrong time. Wrong person, right time.”

    That and… I must say, I’m (finally!) in the arguably enviable place in my life where time and place is no object. By that I mean, I can go anywhere at anytime, and it’s purely delicious (though sometimes a tad overwhelming) to consider the many possibilities.

    Presently… After 2+ years living here in Southeast Asia, I’ve decided to resettle in South America (mainly ‘cuz I speak Spanish a wholeheckofalot better than I speak Vietnamese or Thai) 😉 I actually considered Columbia, but have pretty much now settled on Ecuador (and nope, NOT the expat darling “Cuenca” – toO many farangs for my taste) More likely a smallish Andes town like Loja or Cotacachi.

    ANYWAY, air-wise, I have many options for getting from here (Thailand) to there (Ecuador) and at first I was getting around $1,200 o.w. no matter if I went via my ol’ beloved Seattle, or JFK or whatever. THEN, I suddenly decided that maybe I’d like to gawk at the Taj Mahal before I leave Asia (likely for good), so… I checkED fares from BKK to Delhi to Ecuador and… the bundleD fare was less than $1,100! In short, I could see the Taj for FREE! 😉

    My favorite air sites for such freeplay (foreplay?) include where I can simply peck in “Bangkok to Ecuador February” and it will spit out the lowest fares to various cities. But Skyscanner is my favorite with lots of search options (i.e. for whole month of February) plus handy links to the all the details.
    Dyanne@TravelnLass recently posted..Catching up on Nepal: BhaktapurMy Profile

    • CB Driver
      December 30, 2013 | 8:42 am

      I am SO happy to hear that you’re going to settle in Ecuador–that’s awesome–and it makes sense that you wouldn’t go to Cuenca. Muchos gringos there, for sure. I remember having breakfast at a certain place (which made incredible French toast for prices close to what I pay here, btw) and seeing all gringos except for a plastic surgeon. :) Anyway, if you’re there in the future, I hope we get to meet. I’m sure I’ll be returning!

      I love that you can get to see the Taj free via that flight. Very cool.

      Freeplay/foreplay? Ha ha ha!!!! That’s great.

      Good to know about Skyscanner.

      • Dyanne@TravelnLass
        December 31, 2013 | 11:11 pm

        Yes Lisa – when you mentioned “Columbia” above, I was hoping (still am) that we might somehow rendezvous down south.

        And yes too, about that French toast 😉 Alas it’s the same here in Chiang Mai. While there’s certainly plenty of cheap street food to eat, it seems the hordes of expats/travelers don’t realize they’re paying as much for pizza and other Western foods/clothes, etc. – as they do in the U.S. Crazy.

        Don’t get me wrong, I too enjoy (indeed NEED) a bit of Western comfort food on occasion, but… too often in places like Chiang Mai and I think, Cuenca – the demand for such by the huge influx of expats rather changes the landscape of the local culture.

        So yes, I’ll likely be looking at smaller towns (like Cotacachi, Loja, etc.) in Ecuador.

        Crossing fingers that our paths will meet!
        Dyanne@TravelnLass recently posted..​Uh… notice anything different around here?My Profile

        • CB Driver
          January 2, 2014 | 4:20 pm

          Hi, again. Same re: the French toast in Chiang Mai, huh? LOL True how so many ex-pats changes things. I’ve seen that, too.

          That’ll be cool if you end up in one of those towns…I think there’s a good chance we will meet up! :)

  4. Jeruen
    December 30, 2013 | 5:10 am

    Oh Lisa, you always make me laugh with your posts.

    Anyway, I typically have no problems with flight searches, mostly because being so used to traveling and the fact that I am an airline geek makes me aware of the various options that are out there.

    When I was in the US, I mostly used Orbitz, though I would search using other methods (Kayak for example) to find flights. I also knew which airlines fly to where, so I would have an idea what airlines fly the route that I wanted (Wikipedia’s airport articles actually do a good job of listing what airlines fly to which airport; and I used to be an editor of these articles).

    Now that I moved to Europe, somehow most of my recent flight purchases are directly from the airline. So I rarely use third-party online travel agents anymore. It seems that the difference in prices are not that drastic, so I just go directly to the airline to buy my flights. That being said, it is also the case that I haven’t had a long-haul flight since I moved here in September 2012; the last wide-body aircraft I had been in was when I flew from Boston to Munich when I moved to Germany last year.

    There was only one time when I had to change a flight. This was when I wanted to go to Lebanon, but Lebanon denied my visa. By that time, I already booked my flight, flying Berlin to Beirut via Istanbul outbound on Turkish Airlines, and Beirut to Berlin via Cairo inbound on Egyptair. I booked it with my miles on United Airlines. So I had to pay a change fee, but that was relatively painless. And I just rebooked myself on Austrian Airlines, flying Berlin to Yerevan via Vienna.

    I have to say though, I read a lot of fine print. I know my booking code (and whether I can earn miles from it or not, and if so, how much). I guess most people don’t know up to this level of detail, so people immediately assume that meals are included, or seat reservations, or what-not. But with the range of airlines nowadays from luxury class to ultra-low-cost carrier, then it’s just worth to read the fine print and see what is actually included in the price you are paying.
    Jeruen recently posted..Real PosesMy Profile

    • CB Driver
      December 30, 2013 | 8:38 am

      Hey, Jeuruen. Glad I made you laugh! :) Sounds like you’ve done quite well with flight searches no matter where you are, which is great.

      I often use Kayak to do an initial search and then go visit an airline’s site to see what they’ve got to offer.

      I agree re: Wikipedia. Their listings are quite good!

      Anyway, I’m glad you don’t have any bad (airline) breakup stories to share. Phew.:)

  5. Johana
    January 2, 2014 | 1:17 am

    I feel you lisa!.Same happened to me when I was looking for a flight for my mom.I tought I found the one! it looked sexy and inviting, but sadly, I did not see the red flags.After I selected the flight it turned weird, with many stops and long time waiting . Fortunatly, I did not buy it, and I saved myself a expensive, and traumatic divorce. PD.If it looks too good, it may be a weirdo! :0

    • CB Driver
      January 2, 2014 | 4:24 pm

      Hi, Johana. Funny about the ‘sexy and inviting’ flight! I understand the red flag things; sometimes it’s easy to miss them.

      Glad you didn’t have to go through a costly divorce. Would have been awful–LOL.

      Love that PS. Yup!

  6. Anne @ Pretraveller
    January 2, 2014 | 3:49 pm

    Love it! I never thought of booking a flight from this perspective but it is so true!!
    Anne @ Pretraveller recently posted..NEW! Top 40 Australian and New Zealand Travel BloggersMy Profile

    • CB Driver
      January 2, 2014 | 4:25 pm

      Hi, Anne. Glad you enjoyed the post! It was fun for me to write it. Came about as a result of a thread I began on FB–me complaining re: the difficulties of scoring a good flight. :)

  7. Jon Parker
    January 4, 2014 | 4:49 am

    This is awesome and very true. Is there a category for turning up at the wrong airport and having to shell out a small fortune for another flight? When I did that I felt kinda jilted but it was my own fault!

    • CB Driver
      January 4, 2014 | 10:41 am

      Hi, Jon. That’s funny! Hmmm. I wonder what we can call that. ‘Late to the Date ‘n’ Paying Twice’? :) Thanks for sharing, and I hope you recovered from that experience.

      • Jon Parker
        January 4, 2014 | 10:52 am

        I like it! Great blog, keep up the good work :)

  8. Jeska
    January 16, 2014 | 12:20 pm

    hahaha, this was a hilarious post!
    Jeska recently posted..Snorkeling on OahuMy Profile

    • CB Driver
      January 16, 2014 | 9:57 pm

      Glad you got a laugh out of it! :)

    • CB Driver
      January 20, 2014 | 5:32 pm

      Thanks, Jeska. Glad you found it entertaining! :)

  9. Naomi
    January 21, 2014 | 6:04 am

    that’s a great analogy. So so true. I subscribe to quite a few airlines and hate it when they send you the email deals and I wish I could just take the deal and go. Though I did that last year when I was on holiday in New Zealand and bought a cheap return trip to Bali and then decided where the hell I’d go in Indonesia (definitely not Bali BTW).
    I haven’t done any large hops for a long time so haven’t found the flight planning websites very useful, I definitely check the individual airlines, amazingly often you find flights that don’t show up on the big flight search sites. I guess I’m a bit picky over my men .. ahem.. flights!!
    Naomi recently posted..The Seven Kilo Challenge Part 2My Profile

    • CB Driver
      January 26, 2014 | 4:37 pm

      Hi, Naomi. Glad you got a kick out of this! :)

      Those darn deals they send you…yup. Not Bali? I get it. :)

      True about the individual airlines…and good you’re picky about…both the flights and men. Ha ha! :)

Leave a Reply to CB Driver

Wanting to leave an <em>phasis on your comment?

CommentLuv badge

Trackback URL

Like this blog?

Get my book!


follow the bus

Join Our Facebook Fan Page



don't miss the bus! sign up for the monthly newsletter
Chicken Busology
Learn more about chicken buses by checking out these links:

Chicky Bus: The Real Story: Join me on a wild 12-hour chicken bus ride through Central America. Meet cheese smugglers and other characters. 

Chicken Bus Q & A: I answer all the questions you might have about chicken buses, but were afraid to ask. 

Want the quick fix
Watch the YouTube video to the right of this box. Vicarious thrills guaranteed!

come ride a Chicken Bus