Real Men, Real Dates: Went On A Date With A Girl 17 Years Younger; She Called Dating 'Older Men' Like Me Charity Cases

The world of dating apps can often introduce us to some bizarre situations. Here is a story in our dating series "Real Men, Real Date", of a man who loved dating much younger women through dating apps, until she threw a shocker at him.
Real men real dates

Picture Credit: Canva

As a 39-year-old unmarried man who has been having fun through the world of dating apps throughout my 30s, I've found myself drawn to relationships with women significantly younger than me. Before you judge, hear me out. These women have often been just as eager for adventure as I am, enjoying the experiences I offer them – fine dining, luxury outings, and a lifestyle they may not have access to otherwise. It's been a pattern for me, until I met someone who challenged my expectations.
Last month, I matched with a 22-year-old woman. Yes, a significant 17-year age gap. Despite my initial reservations, she expressed genuine interest. My intentions were always clear from the start – casual fun without any expectation of commitment. Our conversations quickly escalated into sexting, and she eagerly pursued a physical meeting.
Assuming she was like the others, desiring lavish outings and indulgences, I agreed to meet. But she didn't want to go to any fancy clubs and insisted on meeting me at home. I was confused and wasn't sure if I should let her enter my space. But, I gave in eventually. However, when she arrived at my doorstep in a luxury SUV, it became apparent she wasn't after material pleasures. Her choice of transportation spoke volumes because that car costs a bomb.
As we shared dinner at my place, I couldn't shake the question: Why would a young woman with her own means and attractiveness seek the company of a man on the cusp of 40? The night unfolded as expected, the physical connection between us undeniable. Yes, the sex was great. Yet, her true motives remained elusive.
It wasn't until the morning after, as she prepared to leave, that she made an unexpected request. She asked for ?100. Confused, I obliged, only to have her reveal her fantasy – to experience the role of a prostitute. It was her kink, she explained, a way to fulfill her desires. And dating older men? She called it an act of "charity." Yes she called sex with me a charity case, because an "old man" like me would never be able to find a young and sexy girl like her. And that's the reason she does this charity for the older men on dating apps.
Stunned, I was confused with the revelation. I could only understand that she dated, "older men" like me because she felt sad for their situation and this was her act for charity for them. Her words, prompted a deep reflection on my own choices and the dynamics of our encounter. It was a wake-up call, leading me to reconsider the age preference setting on my dating app.
Real Men, Real Dates can be reached at lifestyle.timesnow@timesgroup.com.
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