10 Times When Being Single Stinks

In Advice and Encouragement, Single by Debra Fileta17 Comments

What would you say are the 10 worst times to be single? I had actually been thinking of writing a post addressing some of the struggles of singleness- when I ran across this post at SingleMatters.com by a young man named John Gunter. I thought it was so well-said, that with permission, I asked to repost for your reading pleasure! How true are these? — Deb 

As I type this, I have 4 hours and 50 minutes to go on this flight. Not too bad, except for the fact that I have already been on this airplane for over 9 hours.

Unconscious bodies are strewn everywhere, with only the flicker of seat-back movie screens cutting through the darkness. It is 3:29am where I departed. Yet I am not asleep, as I almost never sleep on planes.

During times like this, I hate being single. I travel a good bit, and I’m often on long flights like this one. Always traveling alone makes trips like this one much more brutal than they already are.

So in honor of traveling alone as a single guy, I’ve compiled a list:

10 Times When Being Single Stinks

Being sick – I HATE being sick while living alone. Add to this the fact that I live in Asia, where I don’t have a CVS down the street or a Publix from which to buy chicken noodle soup, and sickness is absolute misery. Long days of lying incapacitated on my semi-comfortable couch, with no one to interact with, is the worst. Definitely not a benefit of singleness.

Holidays – Holidays really are meant to be with family. When you get well beyond college and you’re still not married, holidays can be sad. Thankfully, I have always had great communities to fit into over here for holidays, and a wonderful family environment when I am in America. However, I know holidays can be particularly difficult for many singles.

Family style meals – Almost all of the restaurants here in Asia are family style. Being single makes it both awkward and inconvenient for me to eat out. Awkward in that NOBODY here eats alone in restaurants. Inconvenient in that I can either order two dishes and have way too much food, or order one dish and have an overabundance of one type of food. Do I feel like chicken? Well, that is all I will get. What about beans? While they’re good, I don’t care to make an entire meal out of them. Order both and I get enough for three. Not cool.

Going to romantic comedies – Okay, true confession … I like romantic comedies. I’m not proud of this, but it’s true. However, there is NEVER an acceptable time for me to call a male friend and invite him to join me for a chick-flick. Inviting another dude to a Julia Roberts and/or Hugh Grant movie is grounds for a throat kick. This can never happen. Never.

Pretty much every first conversation I have with people over here in Asia – You just don’t see single men aged 30-plus in Asia. People just don’t know what to do with me. “So you’re 40 AND don’t have a wife? Are your parents worried? You must have many girlfriends! I know a girl you MUST meet …” It’s always an uncomfortable conversation. Half the time I just lie and tell people I have a girlfriend in America. It’s just easier than answering and dodging all the questions. (Read 15 Really Annoying Things Singles Hear).

Nights – Beyond the obvious, it just gets lonely being alone at night in my apartment. I’m not good by myself. I am an extrovert. It gets really old retreating to an empty apartment and waking up in said empty apartment day in and day out.

Moving – I have now moved 17 times in the past 15 years. Brutal. The longest I have lived in one home during that time span has been 22 months. I hate moving, and doing it as a single seems to only be more depressing.

Couples skate at the roller rink – Okay, so I haven’t been to a roller rink since middle school. However, I really hated being forced to sit on the bench while the “couples” got the floor to themselves.  They got the cool spotlights, while I was forced to hammer snow cones on the side watching.  Actually, snow cones were awesome, but not as awesome as skating hand-in-hand with a girl while “More Than Words” blared over the sound system.

Lightning-fast DTRs – It seems to me that when you turn 30, expectations while dating skyrocket. Gone are the days of casual dating and just “spending time with friends” of the opposite sex.  After 30, you are now in the “I don’t want to waste my time with people not serious” mode.  Now you want to know exactly where this thing is headed from the get go … or at least it can feel this way. Personally, I am not a fan of this change. I was never a fan of casual dating. However, I really don’t like feeling I need to have compatibility issues completely ironed out by the end of a grande latte either.

Attending plays and other cultural events – Closely akin to romantic comedies, plays and other such cultural events are just not something you can call your guy friends up for. This stinks for me, as I really do like concerts and plays of all varieties. I’m just not able to call up friends and drag them along. No problem with sports, but “Phantom of the Opera” at the Fox Theater in Atlanta is out of the question! This has led me towards a few uber-awkward blind dates over the years.

Well, that is a good place to start. There are advantages to being single, but these are things which are not cool.

I would love to know your thoughts in the comments section below!

Liked this article? Read more about love, dating, and relationships at the True Love Dates blog!

John Gunter grew up in Atlanta, Georgia, but has lived in East Asia for most of the past 15 years. John loves his life in Asia but misses his family, friends, church, baseball and bar-b-que (in that order) immensely. He enjoys scuba diving when the time and location permits. John blogs at http://JohnGunter.net on issues of faith, purpose, singleness and Asia.

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17 Comments on "10 Times When Being Single Stinks"

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Weddings where there are are very few other singles there and for some reason the DJ decides to play a lot of slow songs. It’s just awful.


When I want to go to that cool event/baseball game/party/concert!….but all my friends are busy with their spouses…:/ so I decide to stay home again to watch reruns of “Say yes to the dress”


Couples skate. Yes! That was one of the loneliest events of my awkward middle school life. Everybody coupled up so I’d make a break for the bathroom or pizza counter.

You mentioned holidays– surprisingly July 4th always seems hardest on me. Fireworks seem so romantic. Maybe it’s everyone sitting snuggled up on blankets and the warm summer air. I don’t know, but it’s a killer.

Amusement park rides.

Married friends inviting me along with them on family outings.

Grocery shopping.

The list goes on! Great job! Really enjoyed reading it.


going out is almost impossible alone.


Lol good one. He ironed out ‘our frustrations’ in one post.


Getting home after a long day of work :/


One of my worst times being single was when all of a sudden all my closest friends were in relationships, and I’d feel like I was hindering their quality couple’s time if I suggested we hang out like we used to. Or I’d find out that they organized fun times together as couples without me. Felt isolated for a bit there but then found other awesome single people to get to know:)


You forgot the other 11,428 times…



Great points. And I like that your article is peppered with humour. Being single is a true burden at times. The struggle is real and you’re not alone. Best wishes to you.

Scott M.

Thx for sharing. I can relate to a lot of what u mentioned. For one, like when I just want to “hang out” with a female friend. I think it does matter what level the friendship is at before “hanging out” because if the degree of friendship is kind of nebulous, (i.e. “just friends” or “friends with a potential for more than friends”), then it could become awkward. I hope this is clear. Any thoughts?

Jennifer Y.
10 times being single is amazing!! 1. When you get invited somewhere, you don’t have to consult another person & see if he/she wants to go. 2. you get the bed all to yourself 3. you can watch whatever you choose on TV 4. no one makes the mess in your home but you 5. no one gets mad at you for NOT making dinner 6. you don’t have to shower everyday (come on, admit it!) 7. you can do whatever you want with your money 8. you can live where ever in the world you want 9. if you… Read more »

It used to really suck, especially because everyone i knew was marrying or married so when i wanted to go out they couldnt really have me around anymore. But i respect that am used to it. Also im last. Most of my friends are marrying, im last so you know. I just try to stay away from couple oriented events generally bc it just reenforces where i am in my walk i do try to pray for couples tho

Jenny Foster

I would have to add a big one for me. It’s vacations and get-aways.
While I LOVe traveling alone most of the time, there is just something missing every time I arrive somewhere beautiful and it’s only me there enjoying it.
I quit my job last year to travel the world (as a photojournalist for several companies) and I love being able to see the world. But, a companion is definitely missing.
Long flights, hotel rooms with just me to enjoy them, walks on exotic beaches, dinners by myself… it get’s extremely lonely.
and it sucks


I just read this email. I totally agree.
It’s not easy living in Asia, yes, most people are married by age 30 nowadays there.
I’m Asian myself and know how it feels while still single and living in Canada!


Being single most certainly has it struggles and it isn’t always easy. Most of my friends are either married or have a sig other. I don’t see them much. In this day and age, it is tough to make friends no matter what I do. The loneliness can get to be too much most days.

Becky Van Dyke

The quiet time of the day, when no one asks about my day, no one is there for me to kiss. The simple everyday things that couples take for granted. That’s the hardest part of being single.

Mellisa Aye

My scariest moments are when i fall sick and cant find anyone to take me to hospital, prepare me a meal or even just keep me company.
Then there are the lonely days festive season,weekends and public holidays when everyone else is busy and none has time to even go out for lunch or catch a movie with me.