2.0 for the Road

2.0 for the Road

After meeting someone new in my life two years after my husband died and dating for almost a year, we decided to take our first trip together to New York City. The impetus was to hear my younger son, a musician, perform and also visit my two sisters who live in the Big Apple. What better way we decided to test our relationship than travel a deux. This would be a close, personal look at how each of us handles the stress of travel, dividing expenses, potential conflict from crowded airlines, rude taxi cab drivers, brusque wait staff, the discomfort of sharing a single hotel bathroom…and so on. You get the point. It’s not easy becoming two peas in one pod 24/7.

I was certainly skittish, having never traveled with a man other than my late husband or father. In addition, what would I tell my prudish 90-plus-year-old mother when I disappeared for a week with my guy friend? This is the person who, when I told her about him, immediately envisioned a big sparkly diamond ring on my finger and a march down the aisle. Getting married again, I had told her many times, was not something I wanted, at least at that time or even now. “Why do so at my age? It’s a new world, mother,” I said emphatically, almost in a lecturing tone. I didn’t have to justify my decision to her as I mumbled to myself: “Margaret, grow up. You’re in your sixties. Go for it, have fun, you deserve it.”

Before the guy and I boarded the plane, I knew it would be necessary to set some rules in advance such as where to stay, eat, acceptable price points for both of us and who would pay for what and how, sights not to miss, modes of transportation… and so on. Here are a few ways I learned to prepare for travel for the first time with my special partner, as I started to refer to him, and which can guide you if you’re single, past 50 and just starting these types of adventures.

Destination and how long. What do you like to do on vacation? Sightseeing, visiting churches and museums or lying on a beach soaking up sun while reading a fabulous beach novel and sipping a fancy rum drink with a colorful umbrella stuck in it? A trip can combine both. Do you like to go to one city at a time to absorb all the sights and sounds like my guy friend likes to do, or like me, move around doing 10 cities in 10 days? Before selecting a destination, decide how many days you can be away from home, family, your job? My guy is retired and can be gone for as long as he wants. I can’t be away too long with deadlines looming and my 92-year-old mom who’s not well and depends on me almost daily. So we compromise. Maybe we can’t travel as far away or go to as many places in a short time, but for him, we can spend our time in one spot.

Do your due diligence together. Are you a planner and researcher or do you do best with off the cuff routine? What about him? Split up the work, based on each partner’s strengths and interests, and then come together to make a final decision. You book the airline, and he books the hotel. You research tours and attractions. You find out about costs and shopping. He checks out the best beaches and accommodations, shows and concerts. Hotels or Airbnb? Together, you might select good restaurants if you’re both foodies. Do so based on budget. Put the choices on your respective wish list in front of each other and then pare down. You plan day one and he plans day two and so forth. From there, come up with your final itinerary and schedule. And remember, nothing’s ever about 50/50; life isn’t so neat and tidy.

Personal habits. You get up early and fall asleep early; he likes to sleep late and stay up late. He needs a nap in the afternoon; you can’t sleep during the day or you’ll be up all night. You shower in the morning. He showers at night. He likes to eat a big hearty breakfast. For you, a coffee and croissant will suffice. You’re fast; he likes to futz taking his time in the bathroom, dressing or lingering long at a museum where he stops and studies each painting or sculpture, then comments about it to you and anyone nearby who will listen. This is the perfect opportunity to learn to bend to each other’s quirks.

Allow some wiggle room; you are not attached at the hip. It can be challenging to spend 24/7 together. It’s okay to go your own way for a half day. Perhaps, you have relatives in the destination of your choice and you pay them visit while your partner goes to see another church or just sits on the beach soaking up the sun and scenery. Spending time apart allows some breathing room and will help to avert those squabbles that can pop up when two people are together 24/7, which they’re not used to doing back home. Ease into your togetherness as you evolve as a couple. Going your own way also allows you to do what you want to do without having to worry about your partner getting bored or unhappy with your choices.

Talk money and who will pay for what. What about where to stay? Is price a consideration and what are each of you willing to spend? If you split costs, the bucks can go further. Set a budget much like you do every month for your living expenses. What is the most you’ll spend on a hotel? A lunch? A dinner? A play, concert, opera or ballet? Are you splitting everything? Each paying for your own airline ticket, train fare, car rental and sharing the cost of gas if a car trip? Are you paying for the airline tickets and he’s paying for the hotel? For food do you go Dutch? Or does he pay for all then once you’re home and all the bills have arrived, you write him a check for half or whatever you’ve agreed on deducting the cost of the gorgeous pair of earrings he treated you to or the massage and facial you purchased for him. Perhaps, he’s paying for the entire trip if it’s a special occasion and all you need do is pick up the airfare or a special meal here and there. When it comes to costs, be sure to factor in museum passes and other admission fees if you’re trying to be really equal and fair. But again remember there’s a potential danger in trying to be overly even/Steven; you’re a couple not an accounting problem or case study.

How to handle setbacks. This is when a sense of humor is invaluable. Perhaps, that synagogue you always wanted to see is closed. The fabulous restaurant you both wanted to try is booked; you should have done your research and booking in advance. The train you were catching is late or you missed your flight connection. You get lost and don’t speak the language. No one understands English so you take out your little dictionary and attempt to speak the native tongue, and he’s so so so embarrassed. It’s such an awful attempt; you both at least end up laughing. A trip together is supposed to be relaxing and fun. You aren’t beholden to anyone or any schedule that can’t be changed. Ask yourselves when there’s a glitch, What’s the worst that can happen? You lose out on something you wanted to do or see. But remember, there will be a next time if you laugh and move past this. These are the experiences from which great memories are made and one day you’ll sit back and recall the day you took a ship in the opposite direction and discovered a lovely new place.

Surprise your partner. Plan a treat….divert from your itinerary—a picnic with a bottle of wine. Tickets to a Broadway matinee. A fancy, formal dinner that you pay for. Or just spend an evening sitting on a balcony or in a café people watching, enjoying a city at night while sipping a yummy bottle of wine that you hid in your suitcase for the occasion.

Talk about being with others. How much do you want to be just together or with others? Some folks in a relationship have very different ideas. Decide in advance. In our case, we were seeing my son and sisters, as well as having dinner with my writing partner Barbara who was also going to be in the city during the same time, but we didn’t want to spend all our time with others. Tell others; this is our first trip and we’re trying to get away alone. Most will understand.

Talk about those photos and selfies. Some love snapping photos of each other in front of a favorite museum, church, restaurant, or having strangers take shots of them clicking their glasses and downing their fabulous glass of Sauvignon Blanc. Others hate how they look in a photo and don’t want every meal and morsel of food captured. Decide this together, too.

If you communicate your expectations clearly before your airplane takes off, there’s a greater chance once you’re back home, you’ll find you’re still happy to be together and quickly planning the next getaway. By the way, the planning together is a big part of the fun.

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