Sta Hungry Stay Foolish

Stay Hungry. Stay Foolish.

A blog by Leon Oudejans

Possibly Maybe – dating at 50+

Some of you may have noticed that I’ve been dating again since my relocation of early May 2019. I’m not at all fond of dating, given the required high amount of input compared to its meager output. I minimise both online chats and face-to-face meetings, by having (long) phone conversations with “possibly maybes”. Usually, this strategy is successful.

Within a couple of days after registering online, I was approached by a woman who wasn’t even in my search results. Perhaps, that should have been an early warning. Nevertheless, she really got my hopes up high. Three weeks later, I was dumped. She explained we were “too different”. I was flabbergasted as I didn’t see it coming, although I felt something was wrong.

One of my face-to-face meetings resulted in my recent blog: One question says more than a thousand answers. My subsequent blog, Friendship is a goal for women and a tool for men, resulted from an epiphany during one of my long phone conversations. The “too different” argument will soon result in a follow-up on my 2018 blog: Why do opposites (not) attract?

My dating results of the past two months are mixed: some nice people, some disappointments, some boosted my energy levels while others were a drain. Also see a 2019 article in The Cut: I Hate Dating Apps So Much! Unfortunately, dating often feels like an attack on Hope itself. Currently, I’m back at the beginning of the circle of Doubt-Fear-Hope-Love (my blogs).

I’ve been wondering why dating is hard at 50+. In the words of my recent blog: Age does matter. Dating at 50+ is likely to involve unresolved history (eg, death, divorce, F/M mistrust). Its “scars” will be revealed in time: either in the very first meeting, or after weeks/months.

The most surprising question that I received was about the present: are you healthy? I laughed but she was dead serious. She gave me a long list of her medical issues. Various women told me that men frequently lie about their age, health and intentions (eg, attention, friendship, sex). One guy even turned up in a wheelchair without having informed his future date.

Quite often, there is misalignment about future intentions. Many people are unwilling to relocate and giving up their independence (eg, family, friends, house, job). Hence, the most you can expect is a LAT relationship; forget about cohabiting or marriage. Everyone wants her/his personal space and time (my 2017 “Me time” blog). Some conversations even make you wonder if there is adequate time for a (starting) romantic relationship.

The upside of dating at 50+ is that the ocean is full of fish. This is also its downside. The next person on the website might be your ideal romantic partner and else the following one. As a result, we either go for ideal or for nothing. There is no compromise between ideal and nothing. Hence, my 2018 blog: From dating to swiping to nowhere?

The pitfall of dating is that even confident people will start feeling uncertain. Possibly maybe, dating including its share of disappointments, makes us feel that we are losing control. Its upside is, that it happens to all of us. I suppose that makes us human after all (artistlyricsvideo).

Possibly Maybe (1995) by Björk
artist, lyricsvideo, Wiki-1, Wiki-2

Your flirts finds me out
Teases the crack in me
Smittens me with hope

As much as I definitely enjoy solitude
I wouldn’t mind perhaps
Spending little time with you
Sometimes, sometimes

Note 1: all markings (bold, italic, underlining) by LO unless stated otherwise

Note 2: hat tip to AvdH for mentioning the expression “possibly maybe” to me


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