Ask Wendy

Can I Ask My Long-Distance Guy to Send Me an Airline Ticket?

Friday, July 26, 2019
map and two people
Hey Wendy,

I’m a single mother starting to get involved with a man who lives across the country for now. This man owns a condo in my city, and he’d planned to move into a nearby townhouse when we met, before realizing that his obligations would keep him back east.

He has expressed that he’d like to spend time together to see if we would have a future despite the distance (my youngest has 4 years of high school left, so I couldn’t move before then).

He has been really attentive and said that I should come to see him in New York.

My question is: can I ask him to send me a ticket (he can certainly afford it!) or should I buy my own this early on? Also, if I buy my own, is he investing in the relationship enough? Please advise...

Lisa — San Diego, CA

Hey Lisa,

Remember when you were a teen and you told your friend, “you fly, I’ll buy”? They grabbed the burgers and fries so you didn’t have to get your lazy bones off the couch, but for their effort, you paid for the fast-food run.

This is the grown-up version of that. You fly, he buys—literally.

When you take a trip to New York to visit him, you are investing your time and energy by temporarily putting your life on hold. You’re sorting out a schedule and back-up adult supervision for your teen. You’re juggling your routine around and cramming chores in days prior just to make it all happen. You’ve got transportation to and from the airport, the schlepping of bags, and the noise and hassle of navigating through the airports and on the plane. There is value in that, and I’d say it’s at least the price of your roundtrip ticket.

So yes, he pays, and make sure he doesn’t stick you in the cheap, center seat. When you’re sorting out dates that work for you both you can say, “There’s a lot to juggle on my end to make it work, but I’m excited about the trip. Are you willing to pay for my flight and come fetch me from JFK?” You want to be that direct about it. And if you get pushback because he wants you to pay plus put in all that effort? No. Just no.

So, when the first trip goes well, and you two crazy lovebirds decide you want to see more of each other, you need to spend real time together. Before anyone packs a single moving box, make sure you’ve spent at least three consecutive weeks together, preferably in the town you’ll be living in together. You need to see how each other moves through the world, responds to problems, and handles life’s little challenges. How long does it take for his “patience tank” to run down to empty? And when it’s low, how’s he treating you and those around you? Does he have grace or is he snappy? Everybody’s an asshole sometimes. You need to discover what flavor of asshole he is, and see if it’s workable. You’ll likely never get to see any of this on weekend getaways and through your telephone or video chat relationship. You need this intimate knowledge about him before moving—even if you’ve been dating for four years.

In your letter to me, you say he has a condo in your town, but you mention you won’t be able to move with him for at least four years. Are you considering moving to New York? If I get a vote, I say the person who’s more familiar with their love’s town moves there. You know, the one who owns a condo and likely has connections in said town? Uprooting your life and your child’s life to move across the country to a place where you don’t have any community is not my favorite plan for you.

Thank you for sending me this question as a part of my book giveaway—you are one of the winners! I’ve likely mailed you a signed copy of 121 First Dates by now, so check your mailbox and please give it a read! I have so much more for you in my book about dating long distance, and what you need to look for in your potential mate before you determine whether he’s your one.

Good luck!



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