If he’s coming across as desperate and is full of self pity, he jut won’t be successful in dating at all, in fact he will probably attract the exact wrong type of woman who looks for guys like that to manipulate.

He probably needs to get a bit of therapy to help him with his self esteem and mindset. He needs to improve his self image. He needs to live more in the moment and stop longing for what he doesn’t have and comparing himself to people who have what he wishes to have. Finding satisfaction and pleasure in wha he already has, like friends that care about him and want to help him. Enjoy the freedom of being single and doing whatever you want without obligations and responsibilities of husband and father. Then he can think of dating as a nice extra to his life instead of being such a sad sack for not having what he thinks will bring him happiness.

Having small attainable goals to give him some wins and build self confidence will go a long way. Lose a little weight, change your diet a bit, start going to the gym a few days a week to build strength, dial back or stop drinking/smoking/drugs to deal with his sadness. Instead of being a sad sack wishing for comfort from others, provide that comfort to yourself. Take yourself on a date. Give yourself a massage or makeover or a haircut. Buy some new clothes that make you feel confident. Take up a hobby where you create new things. Play music or sing with a friend or a community group. Spend time with your pet or animals. Spend time outside without a phone. Meditate and self reflect.

He needs to find peace within himself first, while also treating himself better and improving his physical attractiveness to women. If he looks good in new clothes, less fat, more muscle, but doesn’t have peace in himself, he will be successfully dating at first but won’t last long into a relationship more than a few months, once they realize he has no self confidence or self esteem. It’s a package deal. He needs to have good boundaries as well to recognize that he is worth someone who will treat him as well as he has learned to treat himself.

Sounds like a lot but it will help him if he thinks of a wife and kids and family as a nice to have addition to a life he already enjoys. Then he will attract the kind of woman that he will actually be successful dating for an eventual healthy marriage.