All Woman
  • Home
  • Relationships
  • Features
  • Fashion & Beauty
  • Health & Fitness
  • Your Rights
  • Parenting
  • Advice
    • Home
    • Relationships
    • Features
    • Fashion & Beauty
    • Health & Fitness
    • Your Rights
    • Parenting
    • Advice
Awkward one-night stands
<b/>
All Woman, Relationships
April 23, 2016

Awkward one-night stands

WAKING up next to a total stranger after sharing the most intimate parts of you with them the night before will naturally be an uncomfortable experience. But there are some experiences that have transcended from being merely uncomfortable to embarrassingly awkward, and below All Woman readers share their most cringeworthy ones.

Ceon:

I met this guy, the connection was good, and all I thought about was sex with him once or twice while we danced. Anyway, I couldn’t get a taxi so he said I could come home with him. I accepted his offer without checking to see if this guy lived alone. I tried leaving before he woke up but ran into his mother and sister. His mother, in the rudest voice, and looking at me with scorn, said ,”Look what the cat dragged in”. I was able to laugh about it days later, but gosh I wanted to smack her.

Shana:

After what I thought was amazing sex with a super hot guy who I thought was feeling me as much I was feeling him, the guy rolled over in the morning around the same time I opened my eyes, looked at me and hissed his teeth.

Romane:

It was my third college party and my friends hooked me up with a friend of their friend. We spent most of the night together and she begged me to take her home even though I told her it may not be such a good idea. I should have listened, it seems, as this girl woke up at a quarter to four in the morning screaming, “He stole my vagina!” You can imagine what that did to my reputation.

Britty:

I was studying abroad and my friends and I went to Vegas. I decided to try hooking up with a really hot guy — he looked wealthy too. He took me to his hotel room, nice place, and I even told him what I was studying and so on. We had great sex but the next morning I woke up and gently touched him on his shoulder as I was about to leave. He pointed at his pants and said, “There should be about $500 in my pocket, please leave me with at least $50 as I’ll need to take a cab.” I nearly screamed. I can’t believe he thought I was a prostitute.

Graig:

There is psycho and then there is psycho. You know how at a wedding the single women catch the bride’s bouquet and the men the garter? Well, anyway, it so happens that I caught the garter and the woman who caught the bouquet ended up dancing with me later at the reception, and we eventually went to bed together that night. As I woke up to leave the hotel room in the morning, the woman started asking when we would start dating officially, and how long it would be until the engagement ring. She thought that whoever caught the bouquet and the garter should get married. It was awkward and frightening.

Shian:

I woke up thinking I was dreaming that I had the most amazing sex with an ugly guy with a really great body. I had these dreams all the time. But not only did I soon realise that “my dream” was not actually a dream, but I later found out that the guy was my grandmother’s handyman.

Tonya:

I fell head over heels with one of the interns at work, and convinced my friend to introduce us. That same night we went out for drinks, and eventually ended up back at my place. After what was a disappointing session for me, as he was quite tipsy, he got up, got dressed, and said, “At least the sex was good.” To this day I don’t understand what he meant by that.

Frederick:

I didn’t know she had a kid, seriously, and by the time we got to her place, passion had taken over from wisdom ­— wisdom that would have normally allowed me to see the twin bed in the room. Whether it was the liquor, or her sex appeal that clouded my eyes, I don’t know, but next morning when I opened my eyes, there was a little girl staring at me. Let’s just say I ended up taking the child to school the next morning, and she seemed quite comfortable calling me “uncle”. I never went back there though, as I couldn’t believe that the mother would take a stranger to bed with her child sleeping in the same room.

{"website":"website"}{"allwoman":"All Woman"}
0 Comments · Make a comment

HOUSE RULES

  1. We welcome reader comments on the top stories of the day. Some comments may be republished on the website or in the newspaper; email addresses will not be published.
  2. Please understand that comments are moderated and it is not always possible to publish all that have been submitted. We will, however, try to publish comments that are representative of all received.
  3. We ask that comments are civil and free of libellous or hateful material. Also please stick to the topic under discussion.
  4. Please do not write in block capitals since this makes your comment hard to read.
  5. Please don't use the comments to advertise. However, our advertising department can be more than accommodating if emailed: advertising@jamaicaobserver.com.
  6. If readers wish to report offensive comments, suggest a correction or share a story then please email: community@jamaicaobserver.com.
  7. Lastly, read our Terms and Conditions and Privacy Policy
ALSO ON ALL WOMAN
10 ways for women to continue winning this year
All Woman, Features
10 ways for women to continue winning this year
June 29, 2026
EVERY new season is an opportunity to grow, evolve and become an even better version of yourself. Winning isn’t always about major achievements, it’s ...
{"xml":"xml"}{"allwoman":"All Woman", "jamaica-observer":"Jamaica Observer"}
Ranking the female zodiac signs: Lovers, heartbreakers and walking red flags
All Woman, Features, Relationships
Ranking the female zodiac signs: Lovers, heartbreakers and walking red flags
JEVAUGHNIE SMITH 
June 29, 2026
NO one wants to admit that zodiac signs have a bearing on our personalities; in fact, the responses to my previous testimony that with men, some signs...
{"xml":"xml"}{"allwoman":"All Woman", "jamaica-observer":"Jamaica Observer"}
Hidden wounds: Signs of trauma in a man, that women often miss
All Woman, Features, Relationships
BY MARIE BERBICK
Hidden wounds: Signs of trauma in a man, that women often miss
Marie BERBICK-BAILEY 
June 29, 2026
MEN are not known to be emotional. They often suffer in silence, choosing to act out their trauma rather than address it. And not all trauma in men sh...
{"xml":"xml"}{"allwoman":"All Woman", "jamaica-observer":"Jamaica Observer"}
Hubby confessed to past relationships with men
Advice, All Woman, Features
Hubby confessed to past relationships with men
Christopher Brodber 
June 29, 2026
Counsellor, I returned to Jamaica four years ago after living abroad for many years, and dating a man long-distance. Last year we got married. He’s fr...
{"xml":"xml"}{"allwoman":"All Woman", "jamaica-observer":"Jamaica Observer"}
Passport name worries
All Woman, Your Rights
Passport name worries
Margarette Macaulay 
June 29, 2026
Dear Mrs Macaulay, I went to renew my Jamaican passport the other day, and they refused to use my correct first name. My first name is Ann Marie (spac...
{"xml":"xml"}{"allwoman":"All Woman", "jamaica-observer":"Jamaica Observer"}
Marian Allen’s legacy of impact
All Woman, Features
Marian Allen’s legacy of impact
June 22, 2026
“I refuse to live a meaningless existence. The life I live must be impacting the lives of others positively.” That philosophy has guided 45-year-old M...
{"xml":"xml"}{"allwoman":"All Woman", "jamaica-observer":"Jamaica Observer"}
Mom finding excuses to prevent dad’s access
All Woman, Features, Your Rights
Mom finding excuses to prevent dad’s access
Margarette Macaulay 
June 22, 2026
DEAR MRS MACAULAY, My babymother will not allow our child to visit, even though I recently got a court order that gives me weekend and holiday access....
{"xml":"xml"}{"allwoman":"All Woman", "jamaica-observer":"Jamaica Observer"}
Hubby has his cake, and wants to eat it too
Advice, All Woman, Features
Hubby has his cake, and wants to eat it too
Christopher Brodber 
June 22, 2026
Counsellor,  I am 48 and have been married to my husband, who’s 10 years younger, for 13 years. We basically built each other from the ground up. We m...
{"xml":"xml"}{"allwoman":"All Woman", "jamaica-observer":"Jamaica Observer"}
❮ ❯
Scroll
Polls
10 ways for women to continue winning this year
All Woman, ...
10 ways for women to continue winning this year
June 29, 2026
EVERY new season is an opportunity to grow, evolve and become an even better version of yourself. Winning isn’t always about major achievements, it’s ...
{"xml":"xml"}{"allwoman":"All Woman", "jamaica-observer":"Jamaica Observer"}
Ranking the female zodiac signs: Lovers, heartbreakers and walking red flags
All Woman, ...
Ranking the female zodiac signs: Lovers, heartbreakers and walking red flags
JEVAUGHNIE SMITH 
June 29, 2026
NO one wants to admit that zodiac signs have a bearing on our personalities; in fact, the responses to my previous testimony that with men, some signs...
{"xml":"xml"}{"allwoman":"All Woman", "jamaica-observer":"Jamaica Observer"}
Hidden wounds: Signs of trauma in a man, that women often miss
All Woman, ...
BY MARIE BERBICK
Hidden wounds: Signs of trauma in a man, that women often miss
Marie BERBICK-BAILEY 
June 29, 2026
MEN are not known to be emotional. They often suffer in silence, choosing to act out their trauma rather than address it. And not all trauma in men sh...
{"xml":"xml"}{"allwoman":"All Woman", "jamaica-observer":"Jamaica Observer"}
Hubby confessed to past relationships with men
Advice, ...
Hubby confessed to past relationships with men
Christopher Brodber 
June 29, 2026
Counsellor, I returned to Jamaica four years ago after living abroad for many years, and dating a man long-distance. Last year we got married. He’s fr...
{"xml":"xml"}{"allwoman":"All Woman", "jamaica-observer":"Jamaica Observer"}
Passport name worries
All Woman, ...
Passport name worries
Margarette Macaulay 
June 29, 2026
Dear Mrs Macaulay, I went to renew my Jamaican passport the other day, and they refused to use my correct first name. My first name is Ann Marie (spac...
{"xml":"xml"}{"allwoman":"All Woman", "jamaica-observer":"Jamaica Observer"}
Archives
Polls
Recent Posts
10 ways for women to continue winning this year
All Woman, ...
10 ways for women to continue winning this year
June 29, 2026
EVERY new season is an opportunity to grow, evolve and become an even better version of yourself. Winning isn’t always about major achievements, it’s ...
{"xml":"xml"}{"allwoman":"All Woman", "jamaica-observer":"Jamaica Observer"}
Ranking the female zodiac signs: Lovers, heartbreakers and walking red flags
All Woman, ...
Ranking the female zodiac signs: Lovers, heartbreakers and walking red flags
JEVAUGHNIE SMITH 
June 29, 2026
NO one wants to admit that zodiac signs have a bearing on our personalities; in fact, the responses to my previous testimony that with men, some signs...
{"xml":"xml"}{"allwoman":"All Woman", "jamaica-observer":"Jamaica Observer"}
Hidden wounds: Signs of trauma in a man, that women often miss
All Woman, ...
BY MARIE BERBICK
Hidden wounds: Signs of trauma in a man, that women often miss
Marie BERBICK-BAILEY 
June 29, 2026
MEN are not known to be emotional. They often suffer in silence, choosing to act out their trauma rather than address it. And not all trauma in men sh...
{"xml":"xml"}{"allwoman":"All Woman", "jamaica-observer":"Jamaica Observer"}
Hubby confessed to past relationships with men
Advice, ...
Hubby confessed to past relationships with men
Christopher Brodber 
June 29, 2026
Counsellor, I returned to Jamaica four years ago after living abroad for many years, and dating a man long-distance. Last year we got married. He’s fr...
{"xml":"xml"}{"allwoman":"All Woman", "jamaica-observer":"Jamaica Observer"}
Passport name worries
All Woman, ...
Passport name worries
Margarette Macaulay 
June 29, 2026
Dear Mrs Macaulay, I went to renew my Jamaican passport the other day, and they refused to use my correct first name. My first name is Ann Marie (spac...
{"xml":"xml"}{"allwoman":"All Woman", "jamaica-observer":"Jamaica Observer"}
Archives
All Woman
Jamaica Health, Beauty, Weddings &` Motherhood Stories for the Jamaican Woman.
Sections
  • Relationships
  • Features
  • Fashion
  • Health & Fitness
  • Your Rights
  • Parenting
  • Advice
  • Relationships
  • Features
  • Fashion
  • Health & Fitness
  • Your Rights
  • Parenting
  • Advice
Jamaica Observer, © All Rights Reserved