Late-20s Dating Experience: Part 1

To call it a roller-coaster ride in a volatile minefield would be the most balanced way to describe my experience of dating in the late 20s. It started off well. I had just completed my second degree, and in a pseudo-stable relationship. At 25, I expected to be settling down in a year or two max. Unfortunately, I misjudged that situation and it took longer that it should have to come to an end. You can read all about how I dealt with breakups at that stage here.

late 20s single


At 27, I decided to jump both feet first, back into the dating pool. While I have always had some doubt at the back of my mind on whether marriage and a family would ever happen for me, I desired it in my heart and I was blindly optimistic. My male peers were mostly in a serious relationship, engaged, or married. The dating pool in my late 20s had shrunk, considerably.  The shortage of serious, God-fearing, progressive, respectful men, with no children, who were also truly single, was glaringly obvious. Over 30, bachelors are ‘a little married’, divorcees or with their fair share of drama. Of the eligible ones, very few ticked the essential boxes, yet there were so many of their truly single, ‘great catch’ female counterparts. Men are not oblivious to this crooked ratio; they know.


late 20s


There is a stark imbalance between women who are keen to marry, and men who want the same in their late 20s. This imbalance serves to put women like myself in a very vulnerable position, where we are unknowingly, and sometimes knowingly, pitted against each other in a, ‘The Bachelor.‘ style contest. With every date, I could sense a condescending expectation to prove why I should be worthy to be crowned girlfriend. The pressure to be, ‘pick me’ was at an all time high. Unfortunately being honest and upfront about wanting a family life apparently means you scare men away. The prevailing advice was to downplay my expectations so men don’t feel pressured or rushed or whatever tf.


late 20s pick me


For a time, I feigned nonchalance instead of being honest about my expectations. Before long, my lack of selectivity would find me across a dinner table from a Mugabe apologist, with a MAGA attitude. At that point I just had to ask myself, “Mate, what is this?”. From then onward, I decided to use my truth to separate the wheat from the chaff. A man who doesn’t want the same things I want is a waste of my time. Our paths could never collide and I could never maintain a facade living a ‘pick me‘ life.

I don’t want to get into, ‘not all men’ arguments by discussing outliers. Of course, there are a few decent, genuine guys but honestly in the late 20s, they are needles in the haystack. The haystack itself being the kinda-married men, the divorcee still living with his ex-wife, those with a child or two, the narcissist, and those with immigration issues. Men in their late 20s believe they have options and don’t necessarily want to date exclusively. How do you plan a future with someone who isn’t committed? I never expected to still be dating at my big age but I just knew, this wasn’t it bro.

(….this was getting a bit long so, to be continued!)




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