Why is dating someone out of pity more hurtful than rejecting them?

Anonymous
My best friend once set me up on a date with her co-worker. Let's call him Mike. He was a bit overweight, had a serious case of facial acne, was awkward and kept getting rejected.

Mike was indeed unattractive and awkward but I tried being nice. We went out on several dates, I let him kiss me (then I reciprocated). I kept pretending and accepted to be his girlfriend when he asked me. I tried to do things to bore him. It wasn't working.

Then I guess lucky for me, he overheard my conversation with my best friend. She knew the truth but kept it a secret. We agreed that if I kept pretending to date him for another 3 months, she would pay me $100. He was more hurt, said he would've rather preferred being rejected and never spoke to either of us (even blocked us too) again. He even changed jobs. At least I didn't reject him.

But seriously... wasn't I doing him a favor at least? I was the only one that accepted being his girlfriend. Isn't dating someone out of pity better than nothing?
Why is dating someone out of pity more hurtful than rejecting them?
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