All Woman
  • Home
  • Relationships
  • Features
  • Fashion & Beauty
  • Health & Fitness
  • Your Rights
  • Parenting
  • Advice
    • Home
    • Relationships
    • Features
    • Fashion & Beauty
    • Health & Fitness
    • Your Rights
    • Parenting
    • Advice
5 of the most awkward and embarrassing dates
All Woman, Relationships
June 13, 2021

5 of the most awkward and embarrassing dates

IF you have ever dated before, then you know just how unpredictable and stressful the dating world can be. Having said that, while any date could be the start of something great, the reality is that dates, especially first encounters, are a hotbed for awkward and embarrassing moments.

Have you been riding a lucky streak in the dating arena, or do you have your fair share of cringe-worthy dates under your belt? We asked All Woman readers and rounded up five nightmarish experiences. Check them out below:

Stacy-Ann, 30, teacher:

I struggle with a gastrointestinal issue, but I love pasta. Approaching date day, I was sure to avoid all things dairy for a week, so I thought I was good. I yielded to my temptation and ordered a spicy jerk surf and turf pasta and everything went downhill from there. Not only did it send me to the bathroom three or four times, what made matters worse is that he had picked me up from home and had to drop me back, even though I was releasing stink bombs every 15 minutes. Thankfully, I lived just 30 minutes away.

Shelly, 28, pharmacy technician:

We went to a Greek restaurant in Kingston, and my date seems to have rehearsed a couple of the dishes so he could order. He over-pronounced and the accent was terrible. It was embarrassing.

Latoya, 35, loan officer:

After we sat talking and having drinks for at least an hour, then resumed chatting up after eating dinner, I went to the bathroom to freshen up. While freshening up, I realised that a piece of green vegetable had been stuck to my teeth. It means that while I was out there chatting and laughing, the man was looking at it in my mouth. I thought he was staring at my lips because I always get complimented on how good they look. I was so embarrassed. I barely said anything when I got back from the bathroom and the car ride home was next to silent.

Germaine, 27, IT support technician:

While out on maybe our third date, every time I meant to address her by name, I ended up calling her by her friend’s name. She got annoyed. To make matters worse, I had ordered garlic shrimp and it made my breath smell, and at the end of the date, when she leaned in for a kiss I figured that she got a whiff of the smell. I leaned in just in time before she changed her mind about kissing me. The kiss felt awkward, almost like she didn’t want to. I felt uncomfortable the whole time; she seemed to have lost interest in me, but we went out a few more times.

Keriece, 23, student:

My friend had set up a blind date for me as part of a college challenge. When I went this man was my stepsister’s ex-man. I wasn’t going to go through with the date, but it wasn’t a big deal — it was a nice restaurant plus he and I barely had any prior interactions. Things got weird, though, when he started spilling details about him and my stepsister’s break-up. He went into so many uncomfortable details about her sexual fluidities and demons that I had to threaten to leave midway my meal if he didn’t stop. I didn’t accept his ride home; I have blocked and deleted his contact information, but now it’s difficult to look at my stepsister.

— PENDA HONEYGHAN

{"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
From Jamaica to New York: Netania Mundell’s journey into global marketing
All Woman, Features
From Jamaica to New York: Netania Mundell’s journey into global marketing
June 8, 2026
FEW people would have predicted that a young woman studying accounting at university would one day find herself helping to shape marketing strategies ...
{"xml":"xml"}{"allwoman":"All Woman", "jamaica-observer":"Jamaica Observer"}
Woman endures emotional abuse, threats and financial exploitation
All Woman, Features, Your Rights
Woman endures emotional abuse, threats and financial exploitation
Margarette Macaulay 
June 8, 2026
Dear Mrs Macaulay, I write to you with a heavy heart and because my mother is unable to. My parents have been in a toxic relationship for years and I ...
{"xml":"xml"}{"allwoman":"All Woman", "jamaica-observer":"Jamaica Observer"}
I opened my marriage. Now my wife won’t give up her younger man
Advice, All Woman, Features
I opened my marriage. Now my wife won’t give up her younger man
Christopher Brodber 
June 8, 2026
Dear Counsellor, I went to my wife a few months ago and said we should open our relationship, as when we got together, we agreed that we both were non...
{"xml":"xml"}{"allwoman":"All Woman", "jamaica-observer":"Jamaica Observer"}
Picture Perfect
All Woman, Features, Parenting
Picture Perfect
June 8, 2026
Traiden Lawson celebrated his first birthday in style last weekend. He’s loved by parents Latanya Campbell and Trevone Lawson.
{"xml":"xml"}{"allwoman":"All Woman", "jamaica-observer":"Jamaica Observer"}
Recurrent vaginal infections: Achieving the perfect balance of bacterial flora
All Woman, Health, News
Recurrent vaginal infections: Achieving the perfect balance of bacterial flora
Dr Daryl Daley 
June 7, 2026
SHE sat across from me looking extremely defeated. Sandra, a 34-year-old schoolteacher, was extremely frustrated. This visit to me, made the fourth ob...
{"xml":"xml"}{"allwoman":"All Woman", "jamaica-observer":"Jamaica Observer"}
5 habits of women who inspire change
All Woman, Features
5 habits of women who inspire change
ALAISHA THOMAS 
June 1, 2026
SOME women are constantly celebrated for their ability to bounce back from challenges, empower others, and make a meaningful difference in the world a...
{"xml":"xml"}{"allwoman":"All Woman", "jamaica-observer":"Jamaica Observer"}
Single father loading…
Advice, All Woman, Features
Single father loading…
Christopher Brodber 
June 1, 2026
Counsellor, I was a teen mom who had two children — twins — before my current relationship. Both older kids just graduated high school and will be mig...
{"xml":"xml"}{"allwoman":"All Woman", "jamaica-observer":"Jamaica Observer"}
Flexibility is not a perk, it’s a necessity for working mothers
All Woman, Features
Flexibility is not a perk, it’s a necessity for working mothers
June 1, 2026
FOR generations, Jamaican women have carried two full-time roles at once — building careers while managing the invisible weight of caregiving, househo...
{"xml":"xml"}{"allwoman":"All Woman", "jamaica-observer":"Jamaica Observer"}
❮ ❯
Scroll
Polls
From Jamaica to New York: Netania Mundell’s journey into global marketing
All Woman, ...
From Jamaica to New York: Netania Mundell’s journey into global marketing
June 8, 2026
FEW people would have predicted that a young woman studying accounting at university would one day find herself helping to shape marketing strategies ...
{"xml":"xml"}{"allwoman":"All Woman", "jamaica-observer":"Jamaica Observer"}
Woman endures emotional abuse, threats and financial exploitation
All Woman, ...
Woman endures emotional abuse, threats and financial exploitation
Margarette Macaulay 
June 8, 2026
Dear Mrs Macaulay, I write to you with a heavy heart and because my mother is unable to. My parents have been in a toxic relationship for years and I ...
{"xml":"xml"}{"allwoman":"All Woman", "jamaica-observer":"Jamaica Observer"}
I opened my marriage. Now my wife won’t give up her younger man
Advice, ...
I opened my marriage. Now my wife won’t give up her younger man
Christopher Brodber 
June 8, 2026
Dear Counsellor, I went to my wife a few months ago and said we should open our relationship, as when we got together, we agreed that we both were non...
{"xml":"xml"}{"allwoman":"All Woman", "jamaica-observer":"Jamaica Observer"}
Picture Perfect
All Woman, ...
Picture Perfect
June 8, 2026
Traiden Lawson celebrated his first birthday in style last weekend. He’s loved by parents Latanya Campbell and Trevone Lawson.
{"xml":"xml"}{"allwoman":"All Woman", "jamaica-observer":"Jamaica Observer"}
Recurrent vaginal infections: Achieving the perfect balance of bacterial flora
All Woman, ...
Recurrent vaginal infections: Achieving the perfect balance of bacterial flora
Dr Daryl Daley 
June 7, 2026
SHE sat across from me looking extremely defeated. Sandra, a 34-year-old schoolteacher, was extremely frustrated. This visit to me, made the fourth ob...
{"xml":"xml"}{"allwoman":"All Woman", "jamaica-observer":"Jamaica Observer"}
Archives
Polls
Recent Posts
From Jamaica to New York: Netania Mundell’s journey into global marketing
All Woman, ...
From Jamaica to New York: Netania Mundell’s journey into global marketing
June 8, 2026
FEW people would have predicted that a young woman studying accounting at university would one day find herself helping to shape marketing strategies ...
{"xml":"xml"}{"allwoman":"All Woman", "jamaica-observer":"Jamaica Observer"}
Woman endures emotional abuse, threats and financial exploitation
All Woman, ...
Woman endures emotional abuse, threats and financial exploitation
Margarette Macaulay 
June 8, 2026
Dear Mrs Macaulay, I write to you with a heavy heart and because my mother is unable to. My parents have been in a toxic relationship for years and I ...
{"xml":"xml"}{"allwoman":"All Woman", "jamaica-observer":"Jamaica Observer"}
I opened my marriage. Now my wife won’t give up her younger man
Advice, ...
I opened my marriage. Now my wife won’t give up her younger man
Christopher Brodber 
June 8, 2026
Dear Counsellor, I went to my wife a few months ago and said we should open our relationship, as when we got together, we agreed that we both were non...
{"xml":"xml"}{"allwoman":"All Woman", "jamaica-observer":"Jamaica Observer"}
Picture Perfect
All Woman, ...
Picture Perfect
June 8, 2026
Traiden Lawson celebrated his first birthday in style last weekend. He’s loved by parents Latanya Campbell and Trevone Lawson.
{"xml":"xml"}{"allwoman":"All Woman", "jamaica-observer":"Jamaica Observer"}
Recurrent vaginal infections: Achieving the perfect balance of bacterial flora
All Woman, ...
Recurrent vaginal infections: Achieving the perfect balance of bacterial flora
Dr Daryl Daley 
June 7, 2026
SHE sat across from me looking extremely defeated. Sandra, a 34-year-old schoolteacher, was extremely frustrated. This visit to me, made the fourth ob...
{"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