Dating guy with no job - online dating rejections vs. job rejections Ask a Manager


I would really appreciate opinions on this.

I have been single for the past five years and have settled into single parenthood quite happily. Apart from a brief wobble about things last year I feel quite happy not to bother in future with relationships. I am in my forties and feel its quite okay to say that for now a relationship is not what I wanted or needed.

However, last year during my brief wobble I exchanged emails with a widower in his fifties who seemed nice and we got on great by email but it fizzled out and tbh I didn't think more about it. About six weeks ago I got an email from him just asking how I was and so I replied and we have been happily chatting ever since via email. It has progressed to an arranged meeting for lunch although I have said its not a great time for me at the moment to embark in a relationship. He seems really really nice though and if I am honest there is a small part of me which thinks a relationship might be nice.
He has spoken with lots of love about his family, his sadness at the death of his wife at a young age and how awful her illness was in terms of what it did to her, he says he nursed her at home but said it was no hardship because he loved her. As I say, he comes across as a really nice man.

However, my concerns...

He is not in work...gets a small pension from a past job.....been out of work for the past 20 years but obviously some of that has been taken up with being a parent.
Has older children (late teens and early twenties) are still living at home and from our emails I know they have struggled after the death of their Mum and the older ones have had prison sentences for various matters.
He says he is lonely which I can understand....I guess a few years ago he was busy with his children and now they are growing up.
He doesn't drive.

Would these issues put you off?

I personally like to think I am above material stuff....and tbh the "no money" thing doesn't bother me. However, something about what he says makes me picture a chaotic lifestyle and am a bit wary. My friends (the ones I trust to share this with) are saying "no no no....too much baggage" but surely everyone deserves a chance. As I say it's only lunch and at present as far as he is aware I cannot commit to anything although I have a feeling if he likes me in person his feelings about this will be very different.

Would you avoid a man with this kind of history? Or would you give him a chance?

I am leaning much more to the "give him a chance" side but because people around me are saying "you must be mad" I am starting to doubt myself. He sounds really nice though and it's only lunch.

There are 10 percent more young women than young men going to college each year , and while the average pay of a woman is still lower than her male counterpart, there have never been so many power women at the top of their prospective industries.

He knows that vulvas don't look like two unused Pink Pearl erasers and smell like Bath and Body Works vanilla bean, for one.


Dating guy with no job

Dating guy with no job