All Woman
  • Home
  • Relationships
  • Features
  • Fashion & Beauty
  • Health & Fitness
  • Your Rights
  • Parenting
  • Advice
    • Home
    • Relationships
    • Features
    • Fashion & Beauty
    • Health & Fitness
    • Your Rights
    • Parenting
    • Advice
Dating out of their league
All Woman, Relationships
July 5, 2020

Dating out of their league

WE sometimes enter into relationships knowing quite well that we do not exactly match with our partners. These differences — educational background, social status, occupation, age group — can either become the foundation for a strong relationship, or the wrecking ball that eventually knocks the whole thing down.

But even with the risks involved, these readers still got involved with someone they thought was way out of their league. They share the outcomes below.

Kerry, 27, student:

I never thought I was much to look at; I didn’t grow up with any real role model on how to be ladylike, and I was sexually exposed pretty early so I felt at one point that the only thing I had to offer in a relationship was sex. I also found myself in a few ‘situationships’ with men who had their wives or proper girlfriends, so my self-esteem got pretty low. So at first when my husband took an interest in me I didn’t know how to react because he was so educated, handsome, has a great job, and could basically get any girl he wanted. I was also very insecure, thinking he would leave me for some uptown girl. But it’s been nearly four years now and I’m happy that he could see beyond my shortfalls, even when I couldn’t.

Orandy, 29, musician:

I only know one girl who I ever thought was out of my league — one a those pretty girls who don’t ‘smile up’ with people or even look two sides when she crosses the road, because she knows the cars will stop. But I decided to try a thing same way, because she seemed so exclusive. First of all she was much easier to get than I expected, so that was disappointing. The next thing was that she never had much in her head behind the pretty face — all she wanted to talk about was the Kardashians.

Kristoff, 30, entrepreneur:

I was pursuing a girl on campus about five years ago, only for her to ask my age one day and be told I’m a ‘little boy’. It turned out she was eight years my senior, but you could never tell by looking at her. I kept at it but it never got anywhere. Last time I ran into her she was married to an older man. She is still hot, though.

Sancia, 28, sales agent:

I went to a house party in the hills with my sister’s friend one time and met a guy that I knew, from the first conversation, was too ‘bougie’ for me. But he liked me and he thought I was from up there so I played along. I kept it up for a couple months, but he had this privileged a-hole attitude that I couldn’t stand. He was really nice to me because he thought I was rich, but I didn’t like how he spoke about people he thought were beneath him.

Shanelle, 34, accountant:

I had a huge crush on one of my tutors at school and sometimes I thought he liked me too, but my friends said it was just my imagination because he was so hot. But the moment I passed his class he followed me on Instagram, and I knew what was up. We had a good little thing going quietly for a few months before I migrated. We’re still friends, with occasional benefits.

— CANDIECE KNIGHT

{"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
Tammara Glaves-Hucey: On faith, leadership and becoming her truest self
All Woman, Features
Tammara Glaves-Hucey: On faith, leadership and becoming her truest self
February 16, 2026
IN speaking with the people closest to her, friends and colleagues of Tammara Glaves-Hucey, head of general insurance at GKFG, would say she is faith-...
{"xml":"xml"}{"allwoman":"All Woman", "jamaica-observer":"Jamaica Observer"}
DNA test says he’s not the dad
All Woman, Your Rights
DNA test says he’s not the dad
Margarette Macaulay 
February 16, 2026
Dear Mrs Macaulay, I am a father of four young children and a United States (US) resident. All my children were born in Jamaica, and I am in the proce...
{"xml":"xml"}{"allwoman":"All Woman"}
The dangers of relationship-hopping
All Woman, Features, Relationships
The dangers of relationship-hopping
Marie BERBICK-BAILEY 
February 16, 2026
I grew up watching The Bold and the Beautiful religiously. Some of you just smiled because you know exactly where I’m going with this. Brooke — beauti...
{"xml":"xml"}{"allwoman":"All Woman", "jamaica-observer":"Jamaica Observer"}
Fiancé’s cheat sheet
Advice, All Woman, Features
Fiancé’s cheat sheet
Christopher Brodber 
February 16, 2026
Counsellor, My partner insists he didn’t cheat with his ex because nothing physical happened, but he was texting her in a way that was intimate, and d...
{"xml":"xml"}{"allwoman":"All Woman", "jamaica-observer":"Jamaica Observer"}
The love women deserve
All Woman, Features
The love women deserve
ALAISHA THOMAS 
February 9, 2026
VALENTINE’S Day has a way of shrinking love down to roses, reservations and relationship statuses. But the kind of love wo men need, the kind they des...
{"xml":"xml"}{"allwoman":"All Woman", "jamaica-observer":"Jamaica Observer"}
Surrogate mom now wants access
All Woman, Features, Your Rights
Surrogate mom now wants access
Margarette Macaulay 
February 9, 2026
Dear Mrs Macaulay, My husband and I had fertility issues some years ago, and because we couldn’t afford fertility treatments, I allowed him to be with...
{"xml":"xml"}{"allwoman":"All Woman"}
Father’s paramour showing interest in son
Advice, All Woman, Relationships
Father’s paramour showing interest in son
Christopher Brodber 
February 9, 2026
Counsellor, My mother died a year ago and since then, my father, who is 70, and I have lived alone in the home. A few months ago he moved a young woma...
{"xml":"xml"}{"allwoman":"All Woman", "jamaica-observer":"Jamaica Observer"}
6 things you must know about a man before you say yes
All Woman, Features, Relationships
6 things you must know about a man before you say yes
Marie BERBICK-BAILEY 
February 9, 2026
LOVE has a way of making us optimistic, sometimes dangerously so. When emotions are high and wedding bells are ringing, many women assume that “things...
{"xml":"xml"}{"allwoman":"All Woman", "jamaica-observer":"Jamaica Observer"}
❮ ❯
Scroll
Polls
Tammara Glaves-Hucey: On faith, leadership and becoming her truest self
All Woman, ...
Tammara Glaves-Hucey: On faith, leadership and becoming her truest self
February 16, 2026
IN speaking with the people closest to her, friends and colleagues of Tammara Glaves-Hucey, head of general insurance at GKFG, would say she is faith-...
{"xml":"xml"}{"allwoman":"All Woman", "jamaica-observer":"Jamaica Observer"}
DNA test says he’s not the dad
All Woman, ...
DNA test says he’s not the dad
Margarette Macaulay 
February 16, 2026
Dear Mrs Macaulay, I am a father of four young children and a United States (US) resident. All my children were born in Jamaica, and I am in the proce...
{"xml":"xml"}{"allwoman":"All Woman"}
The dangers of relationship-hopping
All Woman, ...
The dangers of relationship-hopping
Marie BERBICK-BAILEY 
February 16, 2026
I grew up watching The Bold and the Beautiful religiously. Some of you just smiled because you know exactly where I’m going with this. Brooke — beauti...
{"xml":"xml"}{"allwoman":"All Woman", "jamaica-observer":"Jamaica Observer"}
Fiancé’s cheat sheet
Advice, ...
Fiancé’s cheat sheet
Christopher Brodber 
February 16, 2026
Counsellor, My partner insists he didn’t cheat with his ex because nothing physical happened, but he was texting her in a way that was intimate, and d...
{"xml":"xml"}{"allwoman":"All Woman", "jamaica-observer":"Jamaica Observer"}
The love women deserve
All Woman, ...
The love women deserve
ALAISHA THOMAS 
February 9, 2026
VALENTINE’S Day has a way of shrinking love down to roses, reservations and relationship statuses. But the kind of love wo men need, the kind they des...
{"xml":"xml"}{"allwoman":"All Woman", "jamaica-observer":"Jamaica Observer"}
Archives
Polls
Recent Posts
Tammara Glaves-Hucey: On faith, leadership and becoming her truest self
All Woman, ...
Tammara Glaves-Hucey: On faith, leadership and becoming her truest self
February 16, 2026
IN speaking with the people closest to her, friends and colleagues of Tammara Glaves-Hucey, head of general insurance at GKFG, would say she is faith-...
{"xml":"xml"}{"allwoman":"All Woman", "jamaica-observer":"Jamaica Observer"}
DNA test says he’s not the dad
All Woman, ...
DNA test says he’s not the dad
Margarette Macaulay 
February 16, 2026
Dear Mrs Macaulay, I am a father of four young children and a United States (US) resident. All my children were born in Jamaica, and I am in the proce...
{"xml":"xml"}{"allwoman":"All Woman"}
The dangers of relationship-hopping
All Woman, ...
The dangers of relationship-hopping
Marie BERBICK-BAILEY 
February 16, 2026
I grew up watching The Bold and the Beautiful religiously. Some of you just smiled because you know exactly where I’m going with this. Brooke — beauti...
{"xml":"xml"}{"allwoman":"All Woman", "jamaica-observer":"Jamaica Observer"}
Fiancé’s cheat sheet
Advice, ...
Fiancé’s cheat sheet
Christopher Brodber 
February 16, 2026
Counsellor, My partner insists he didn’t cheat with his ex because nothing physical happened, but he was texting her in a way that was intimate, and d...
{"xml":"xml"}{"allwoman":"All Woman", "jamaica-observer":"Jamaica Observer"}
The love women deserve
All Woman, ...
The love women deserve
ALAISHA THOMAS 
February 9, 2026
VALENTINE’S Day has a way of shrinking love down to roses, reservations and relationship statuses. But the kind of love wo men need, the kind they des...
{"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