All by myself: a single woman’s guide to having fun in a world built for couples

Tired of boring dates and bad company, Amy Wu decided to throw caution to the wind and enjoy activities by herself. After wine-tastings, hotel night, spas and other fun things, she wonders why she waited so long

PUBLISHED : Thursday, 08 December, 2016, 5:31am
UPDATED : Thursday, 08 December, 2016, 5:30am

Table for one, I told the server, who swiftly seated me. I thought I’d caught a lightning fast look of surprise when I said “one”. I was all decked out in my black heels and evening dress. “Are you waiting for someone? If so I can be on the lookout,” he said. “A friend might join me later,” I replied, with the emphasis on “might”.

The server’s question wasn’t a surprise. After all, it was a Friday evening, a classic date night, and this was the Carmel Mission Inn, the low key yet swanky Californian establishment owned by Clint Eastwood and located in one of the wealthiest spots in Monterey County.

After a half an hour of sipping a glass of pinot noir, the girlfriend who said she might join me arrived and we fell into lively conversation over mojitos and a generous buffet. We enjoyed a few ’80s tunes played by a live band and then she looked at her watch. “I should head back; where are you parked?” she asked.

“I’m staying here,” I said, relishing the look of surprise. “Just myself. Decided to treat myself after a long week,” I smiled. “Ah, good idea,” she said. “We should all do that sometimes.”

How true. The idea of a weekend getaway solo seems so straightforward, but surprisingly my girlfriends still see it as groundbreaking. A single woman engaging in activities solo: weekend getaways, dinner, films, wine tastings, museums and even amusement parks, still feels like foreign territory. But why such surprise? The reality is that many men travel solo, and even dine and see films alone, and are nonchalant about it. So why should it be different for women?

I can’t recall the exact moment when I decided to take the plunge and do activities alone. It might have started when my ex-husband and I drifted apart and being together became less fun. I had more laughs going to Disney with a group of fellow singles than going with him, and besides, being single allowed us to cut through lengthy lines.

Or maybe it was turning 40 and no longer caring as much about how others regarded me. Or creating a new “live list” of things I really wanted to do – see the glaciers in Iceland, enjoy wine tasting in Spain, hot air ballooning, make a quilt, a scrapbook, eat a chocolate sundae for breakfast, or visit the Vatican.

I’d fast learnt in recent years that it wasn’t as easy to find a “partner” or “companion” in sync with my schedule as it had been in my 20s. Many of my friends were married with kids, others struggled with money or time. My much older friends were often limited by health. My own family, parents and sister, were based on the other side of the US, limited by time.

There were the handful of men who were keen about a weekend getaway or fun activities, but quickly disappeared when I made it clear we would be going strictly as travel companions. And there were the few bitter experiences of travelling with a partner of the opposite sex who just wasn’t much fun to be with. One was a night owl who slept until noon, wasting half the day.

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The alternative, which seemed increasingly stifling, was to just not go. So after a depressing drought of fun experiences and sulking at home, I decided: to heck with it. First I had to erase my fears and beliefs that going solo was uncool. The reality is very much the opposite. I found a steal for a night at the Carmel Mission Inn on Hotels.com. I spread out starfish style on the king-sized bed, enjoying wine and cheese and salami as I watched my favourite films. Earlier in the day I’d already pampered myself with a trip to the Refuge, a getaway with hot pools, cold plunge pools, and thermal waterfalls.

The retreat is co-ed and, as expected, I was surrounded by lovey dovey couples (who could not engage in conversation since it was a silent, phone-free place), but the alternative of not going was not acceptable. I curled up with a book and dried off in front of a fire pit.

The weekend experience was so liberating that I started surfing through deals and steals for luxury hotel rooms for the next time. Why did I have to wait for the potential future boyfriend or next husband to enjoy myself?

With the injection of confidence, I signed up for a day long wine tasting excursion in Big Sur, known for its scenic and rugged coastline. The last time I’d done this was with colleagues, and before that with my husband.

Sure enough the tour was packed with couples, many of them middle age or retired. I quickly discovered that wine tasting solo is an excellent way to make friends. As one of the few singles on the shuttle bus, my seatmate was a fellow single woman, a homeopathic doctor, who also had food and wine tasting on her bucket list. She turned out to be an excellent conversationalist, and we exchanged information and are committed to a girl’s getaway weekend.

I also befriended a retired older couple who had amazing stories to share about their travels around the world. We swapped pictures via smartphone, and I heard from them a few days later about connecting again over coffee. Wine tasting alone turned out to be an excellent way to meet new friends and make new connections – another perk of going solo.

In retrospect, I feel that tackling activities or travelling solo is liberating.

I thought of my former PhD director, who looked hard at me when I asked her one time about what research direction I should take. “Think about it carefully and you make your own decision,” she said. “You are the mistress of your own fate.” Those words often resurface when I feel uncertain about trying something new.

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With a newfound confidence I recently went to a holiday film, Almost Christmas, on my own. This was new territory. In the past I’d reserved holiday films for dates only. I had really wanted to see this film and there was no stopping me. Besides, I’d learned that my own company is much better than bad or even mediocre company.

Now I am planning a solo weekend trip to Portland, Oregon, where beer tasting is on the list along with a holiday bread-making class at the local culinary school. An old friend who is an artist might teach me how to paint a self-portrait.

A girlfriend who has been married for the past 14 years observed that I am very independent, especially for a woman. She was wide eyed when I told her I had a weekend getaway on my own, too. “Wow, didn’t you feel lonely?” she asked.

There were the brief moments of longing for a good companion to share the experience with, but those were offset by knowing I can also enjoy life on my own.

Having experienced both worlds, I’ve concluded that in a perfect world it is wonderful to share experiences with a special someone. But short of the right company, it is fun if not desirable to go on one’s own. Life is indeed short, so why wait to start checking off items on the “live list”.

In this past year, I’ve had dinner, gone on a weekend getaway, had fun at Disney, gone on a wine tasting and watched films by myself. I am confident that my status doesn’t have to limit me, and that I can say “table for one” assertively.

And when I do want the company or to be coupled, I believe there is plenty of that to be found, too. After all, there’s no shortage of people who are hungry to connect with others. There’s MeetUp, there’s LinkedIn, there’s Facebook, there’s church groups, there are casual friends who might just want to join me on the next meal, film, a glass of wine or even a trip. But I have options, and in fact always have.

Amy Wu is a California-based freelance writer. She is an American-born Chinese and spent six years living and working in Hong Kong.