The Solo Issue - Part 3: How To Nail Going Out Alone. By Lisa Ellex

The Solo Issue - Part 3: How To Nail Going Out Alone. By Lisa Ellex

. 7 min read

In this third and final installment of our deep-dive series, we interviewed a few folks over 50—with very different results.

If you’ve been following our three-part solo series, you’ll recall that back in Part One we examined the trend of “couples-only” dinner parties and how “suddenly-singles” are finding themselves excluded from the events they once enjoyed when they were partnered. Needless to say, being left off that invitation list has some of us feeling a bit more isolated these days. At a time in our lives when we really would benefit from the support and camaraderie of all our friends, it seems we’re seeing a lot less of them.

In talking with some PrimeCrush readers for this series, I was delighted to learn that the majority of us are going out alone. Whether it be a long bike ride, a fancy dinner, drinks at a bar, a rainy afternoon in a café, or a night at the movies or the opera, lots of us are taking ourselves out on dates and really enjoying the company! I’ve discovered there are quite a few perks to self-dating. First and foremost, I love that I get to choose the plans– 100% of the time. No more do I sit through those formulaic action films I never enjoyed. Never again will I suffer through eating Indian food because it was my partner’s turn to pick the restaurant. And, oh, how exhilarating it is to be free of the chains of dating etiquette; there’s no need to make conversation, and I can take myself home whenever I feel like it. Self-dating bonus: there’s always the possibility of making new friends!  

I first spoke with Kay, a 58-year-old consultant in New York who mirrors my strong feelings about online dating. “I’ve looked at dating sites and I can’t imagine giving up an evening to go out and meet someone. I’m working a ton and I’m finding I don’t have a lot of free time, and I just don’t want to put aside a night for an online date.” Regarding going out alone, Kay embraces the experience and shares her routine: First, dress fab, not sexy. Second, I don't have more than two drinks. Finally, look for a person standing alone in a social situation (cocktail party, etc.) and invite them to join you. Even better if they don’t look like they fit in with the group, such as an older person at a younger party.”

Next, I spoke with “R,” a 50-year-old healthcare professional who is now divorced three years. Her feelings on going out alone on home turf verses away surprised me.  “I’ll see a movie but I have never gone out to eat alone in the town I live in. It’s on my list. I am still figuring out how to do things myself. Last fall I went to Puerto Rico by myself for two weeks. It was the first time I traveled alone outside of work. No companion. Going somewhere completely alone was a little scary. I thought, ‘Who will I talk to for two weeks?’  But it was transformative! Amazing. That process forced me to start listening for myself, and to put away the expectations of other people and to ask myself, ‘What do you want to do?’  

In Puerto Rico, I had booked Airbnb's, traveling around the island counterclockwise. I like to have a couple of scheduled adventures every few days and leave the rest up to chance. The first couple of days I stayed in a neighborhood in San Juan and went to a grocery store I knew from before and just went to the beach and relaxed and sat on my deck and had a beer and swam. It was just me all day long. Then I went to the mountains to a yoga retreat and two things happened there. Shook me up. First, I decided I was going to go to this lake area and hop on and hop off and have drinks and lunch, but when I got there on a Friday nothing was open. They were just open on Saturday and Sunday. I got in my car and I was hungry so I backtracked 30 minutes to the town I just passed. I went on TripAdvisor and found a place for lunch. I drove and passed it. I missed it. I decided to go to the hotel and see if they would let me check in but said, ‘NO! I need to eat lunch.’  So I circled back around, slowed down, and missed it again. I decided to stop at a gas station and grab something. I realized I had nowhere to go and nowhere to be. No one had to be fed or be kept happy. I said, ‘Just drive around and find the restaurant.’ I drove around again and found it this time. It was such an epiphany for me. It was the first time I listened to my own self and let everybody else out. It was such a revelation to me that I carry around and am always thinking of other people and didn’t even know it. How often in the course of a day am I subconsciously thinking about making people happy? Kids, boss, coworkers. When do I think about what I want to do?  Never!  I knew I had to make room for myself.  

I went to the yoga retreat but I sat at the pool all day long instead of going anywhere. I met a guy at the pool and we talked all day. I thought, ‘What do I want for my life?’ I want to make space for not so much work, enjoying things, find what I’m interested in. And that was really profound. I took that feeling back home with me.

Last was Klara, a 58-year-old HR executive living in a northeastern city, divorced for 16 years. Solo since ending a relationship one year ago, she says, “Going out alone? Not that I wouldn’t. I’m generally fine doing that and have done that in certain times but I’ve become more and more of a homebody. And I'm so busy with work and my social life that I haven’t. It does feel lonelier, but in some ways it feels empowering. I used to live in a big city and I’d be more likely to do it there. I have some single friends in town that most days I can grab a glass of wine with or something. I find some of the women at my age to be really interesting and fun.”

As for our male readers, it seems they really know how to have a good time.  “C,” a 56-year-old Bostonian, divorced six years, is quite enthusiastic about going out alone. “I go to a lot of live music. I’ll see a band in a small place and definitely eat out! I’ll go to the pub and sit at the bar alone and have a couple of Guinness and eat dinner. I don’t go to clubs but I do go to festivals and events. And I’ll go to sporting events, both pro and college games. I love to travel. I’ll get a hotel and drive up to Portland, Maine and spend the day and night and visit with friends.”

“M,” a 55-year-old bar manager and long-time Brooklynite, has been single two years after an amicable divorce. On going out alone he says, “I’ve always been a wanderlust. I walk alone, travel alone, vacation alone. When I get out of work at midnight I’m awake, but most people my age are asleep. If I want to socialize, there's only so many places I can go. When you're no longer in a couple you are no longer part of their outings or routines. But I get to live my life the way I please. It’s definitely more fun and I love being alone.”

Finally, there’s Jay, a 60-year-old restaurateur who divorced ten years ago. He’s equally comfortable in the company of others or going solo. “I’m a happy camper whether I’m in a social setting or totally on my own. I truly enjoy having a dinner date with a lady or with one of my buddies, but if there’s no one around and there’s a restaurant I’ve been wanting to try, I’m there. My friends laugh and call it a ‘busman’s holiday’ but I really do enjoy it. After dinner, I’ll usually move to the bar. If I feel like talking, there’s always someone there who is eager to have a conversation. If not, I usually study the restaurant; the layout, the staff, the whole operation.  As far as travel goes, sometimes I actually prefer to travel alone. During slow times at the restaurant, I just pick up and go. I’ll either book a flight or hop in my car and tour the country. I always start with an itinerary but eventually I’ll go whichever way the wind blows. And of course, go to as many restaurants as possible.”

As for me, I don’t need no stinkin’ couples’ dinner. I’ll be on the couch planning my next self-date, and watching that 1932 classic, Grand Hotel, just to hear Greta Garbo say, “I want to be alone…I just want to be alone.”

Want to read Part 1 & 2 of The Solo Series? Check them out here

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