All Woman
  • Home
  • Relationships
  • Features
  • Fashion & Beauty
  • Health & Fitness
  • Your Rights
  • Parenting
  • Advice
    • Home
    • Relationships
    • Features
    • Fashion & Beauty
    • Health & Fitness
    • Your Rights
    • Parenting
    • Advice
Date someone on your level
All Woman, Relationships
 on February 13, 2023

Date someone on your level

ALAISHA THOMAS 

SO many movies have been shot about successfully dating outside your league that people have romanticised the notion of Cinderella and her prince, or the queen and the frog. On some level the thought of ordinary people getting together with extraordinary people gives us the warm fuzzies, but not many of us know that these are the things of dreams.

In fact, experts advise against dating outside your bracket, your league, your level. Even the Bible warns us to be equally yoked, not just in belief, but also status and compatibility.

“When you go outside your circle, your comfort zone or your bracket — whether this is socially, educationally, religiously or otherwise — you’re adding another layer to the issues that you’re bound to face in your relationship,” said Counsellor David Anderson.

“Not many people want to hear this, especially when they’re in love, but it’s the truth.”

Below, three people share the lessons they took from their experiences with these relationships, with the warning standard across all three stories — date someone on your level.

Ann-Marie S, 44, separated:

I was 36 when I met my husband, and was in the last semester of pursuing my master’s. I had a good career going, was making bank, but wasn’t dating at the time. He was younger, much younger, but I didn’t know at the time. He was relentless in pursuing me so by the time I calculated that he was 11 years younger, we were already in love. Not only was he younger, but he hadn’t graduated high school and was in a minimum wage job. But, he was very mature, ambitious, and could hold a conversation, so I didn’t care. We got married, against the advice of both my family and his. We moved quickly to buy a second home, another car, and he started a business. You’d think that once he started working for himself we would have levelled up, but instead he started to disrespect me. Suddenly he was “too good for this”, I was “too old” to have his kids, and I was boring and he wanted to enjoy his life. A year ago I asked him to leave and he left, because truly, I was OK before him and would be fine after him. Apart from a bruised ego and the inconvenience of having to file for divorce, separate assets, and change my name, I’ve been good. It was good for a while and we truly loved each other, but if I had to do it all again I would have told this little boy to piss off the first time he approached me with his smooth talk.

Martina V, 38, divorced:

We met in college so he wasn’t dunce or out of my league educationally, but spiritually we were worlds apart. Well, at first he pretended to be spiritual and told me that he had been baptised, and even played drums in church. But after we got serious I realised that he was just playing with God. We got married and right after, he stopped coming to church with me. Then he started listening to secular music, got tattoos — including a full-sleeve tattoo — and that’s when I realised that this man had no intention of living for God. We have a child, so that’s hard, but it’s so weird for all of us to see her dad having a midlife crisis while we’re Pentecostal. It’s weird and embarrassing sometimes. I guess he’s an OK guy and a good dad, but if you look at me today and look at him you’d wonder what brought us together if you didn’t know that once upon a time he was different.

Matthew L, 50, divorced:

I was raised to take care of my woman so I always knew that my wife would stay at home while I provided. But, my ex took the trophy wife label to another level and in the process almost bankrupted me. She wasn’t just any careless woman either, she was college-educated, even though she didn’t graduate. I put her in charge of the home and kids and went to work, and everyday she would be online shopping, or buying all kinds of items for the house and kids, and every month the credit cards were maxed out. She was living like she was on Real Housewives, and even when I showed her that my business wasn’t doing as well in some months, she didn’t care. When she booked cosmetic surgery I knew it was time to cut my losses and move on, before she sent me to the poorhouse. She got a lot in the divorce but I didn’t even care, because she’s someone else’s problem now. Any other woman I take up will know the value of thriftiness.

{"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
Superwoman doesn’t exist
All Woman, Features
Superwoman doesn’t exist
5 things every driven woman must do to avoid burnout
Marie BERBICK-BAILEY 
August 3, 2026
SOMEWHERE along the way, many women bought into the myth that being ‘superwoman’ meant doing everything, for everyone, all the time. We wear multiple ...
{"xml":"xml"}{"allwoman":"All Woman", "jamaica-observer":"Jamaica Observer"}
A friend in need of benefits
Advice, All Woman, Features
A friend in need of benefits
Rev Christopher Brodber 
August 3, 2026
Counsellor, I have been in a relationship for two years, and have a close female friend who I have known since prep school. My girlfriend was initiall...
{"xml":"xml"}{"allwoman":"All Woman", "jamaica-observer":"Jamaica Observer"}
Mom alienating dad
All Woman, Features, Your Rights
Mom alienating dad
Margarette Macaulay 
August 3, 2026
Dear Mrs Macaulay, Every time I disagree with my ex, and every time she hears that I am dating someone, she says things like, ‘Don’t bother coming to ...
{"xml":"xml"}{"allwoman":"All Woman", "jamaica-observer":"Jamaica Observer"}
Dr Maria Myers-Hamilton: Helping to shape Jamaica’s digital future
All Woman, Features
Dr Maria Myers-Hamilton: Helping to shape Jamaica’s digital future
July 27, 2026
“I’VE always believed that technology should never be an end in itself. Its true purpose is to improve lives, create opportunities and remove barriers...
{"xml":"xml"}{"allwoman":"All Woman", "jamaica-observer":"Jamaica Observer"}
Estranged wife wants half hubby’s inheritance
All Woman, Features, Your Rights
Estranged wife wants half hubby’s inheritance
Margarette Macaulay 
July 27, 2026
Dear Mrs Macaulay, My wife and I struggled financially for years. She moved out, and about four months after, I inherited a home, a business, and a la...
{"xml":"xml"}{"allwoman":"All Woman", "jamaica-observer":"Jamaica Observer"}
Mistress bothered by wife’s pregnancy
Advice, All Woman, Features
Mistress bothered by wife’s pregnancy
Rev Christopher Brodber 
July 27, 2026
Counsellor, I know I may sound like a fool, but hear me out. Six years ago I started dating a man who was married, but separated. He said he didn’t ha...
{"xml":"xml"}{"allwoman":"All Woman", "jamaica-observer":"Jamaica Observer"}
When things aren’t so great financially…
All Woman, Features, Relationships
When things aren’t so great financially…
Marie BERBICK-BAILEY 
July 27, 2026
FEW things put pressure on a relationship quite like money. Research consistently shows that financial stress is one of the leading contributors to co...
{"xml":"xml"}{"allwoman":"All Woman", "jamaica-observer":"Jamaica Observer"}
Nickeria Smickle: Redefining success for the next generation of Caribbean women
All Woman, Features
Nickeria Smickle: Redefining success for the next generation of Caribbean women
July 20, 2026
NICKERIA Smickle built a company, rebuilt communities after a hurricane, and now wants to prove that there’s more than one way to make it. Ask Smickle...
{"xml":"xml"}{"allwoman":"All Woman", "jamaica-observer":"Jamaica Observer"}
❮ ❯
Scroll
Polls
Superwoman doesn’t exist
All Woman, ...
Superwoman doesn’t exist
5 things every driven woman must do to avoid burnout
Marie BERBICK-BAILEY 
August 3, 2026
SOMEWHERE along the way, many women bought into the myth that being ‘superwoman’ meant doing everything, for everyone, all the time. We wear multiple ...
{"xml":"xml"}{"allwoman":"All Woman", "jamaica-observer":"Jamaica Observer"}
A friend in need of benefits
Advice, ...
A friend in need of benefits
Rev Christopher Brodber 
August 3, 2026
Counsellor, I have been in a relationship for two years, and have a close female friend who I have known since prep school. My girlfriend was initiall...
{"xml":"xml"}{"allwoman":"All Woman", "jamaica-observer":"Jamaica Observer"}
Mom alienating dad
All Woman, ...
Mom alienating dad
Margarette Macaulay 
August 3, 2026
Dear Mrs Macaulay, Every time I disagree with my ex, and every time she hears that I am dating someone, she says things like, ‘Don’t bother coming to ...
{"xml":"xml"}{"allwoman":"All Woman", "jamaica-observer":"Jamaica Observer"}
Dr Maria Myers-Hamilton: Helping to shape Jamaica’s digital future
All Woman, ...
Dr Maria Myers-Hamilton: Helping to shape Jamaica’s digital future
July 27, 2026
“I’VE always believed that technology should never be an end in itself. Its true purpose is to improve lives, create opportunities and remove barriers...
{"xml":"xml"}{"allwoman":"All Woman", "jamaica-observer":"Jamaica Observer"}
Estranged wife wants half hubby’s inheritance
All Woman, ...
Estranged wife wants half hubby’s inheritance
Margarette Macaulay 
July 27, 2026
Dear Mrs Macaulay, My wife and I struggled financially for years. She moved out, and about four months after, I inherited a home, a business, and a la...
{"xml":"xml"}{"allwoman":"All Woman", "jamaica-observer":"Jamaica Observer"}
Archives
Polls
Recent Posts
Superwoman doesn’t exist
All Woman, ...
Superwoman doesn’t exist
5 things every driven woman must do to avoid burnout
Marie BERBICK-BAILEY 
August 3, 2026
SOMEWHERE along the way, many women bought into the myth that being ‘superwoman’ meant doing everything, for everyone, all the time. We wear multiple ...
{"xml":"xml"}{"allwoman":"All Woman", "jamaica-observer":"Jamaica Observer"}
A friend in need of benefits
Advice, ...
A friend in need of benefits
Rev Christopher Brodber 
August 3, 2026
Counsellor, I have been in a relationship for two years, and have a close female friend who I have known since prep school. My girlfriend was initiall...
{"xml":"xml"}{"allwoman":"All Woman", "jamaica-observer":"Jamaica Observer"}
Mom alienating dad
All Woman, ...
Mom alienating dad
Margarette Macaulay 
August 3, 2026
Dear Mrs Macaulay, Every time I disagree with my ex, and every time she hears that I am dating someone, she says things like, ‘Don’t bother coming to ...
{"xml":"xml"}{"allwoman":"All Woman", "jamaica-observer":"Jamaica Observer"}
Dr Maria Myers-Hamilton: Helping to shape Jamaica’s digital future
All Woman, ...
Dr Maria Myers-Hamilton: Helping to shape Jamaica’s digital future
July 27, 2026
“I’VE always believed that technology should never be an end in itself. Its true purpose is to improve lives, create opportunities and remove barriers...
{"xml":"xml"}{"allwoman":"All Woman", "jamaica-observer":"Jamaica Observer"}
Estranged wife wants half hubby’s inheritance
All Woman, ...
Estranged wife wants half hubby’s inheritance
Margarette Macaulay 
July 27, 2026
Dear Mrs Macaulay, My wife and I struggled financially for years. She moved out, and about four months after, I inherited a home, a business, and a la...
{"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