Reply to What to say when the truth will hurt

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[quote=Anonymous]I think since he asked you directly, this isn't a MYOB situation.  But there is a lot of judging in the way you phrase it here.  There are degrees of ambition and desires and it may be he just hasn't found the right match.

I do think rather than directing him "you need to be X Y and Z," it would be better to ask question and listen.  Why do you think your relationships have failed?  What is it you're looking for in a LTR?  What do you think women want?  How do you think you present yourself?  What is your best quality?

For example, we have a friend who might appear unmotivated.  He buys and sells stuff - buys at yard sales and sells online.  He's had a roommate who nearly covers his mortgage.  By many DC standards, friend is not ambitious or successful.  But he does what he wants, he sets his own schedule, and he does work hard - it's a fair amount of time.  But it also gives him a lot of freedom and a chance to do things he likes, which are generally low cost or free.  So you could say he's a free spirit.  But it's hard for him to be in a long term relationship, too.

I think the only piece of hard advice you should give him - after asking him all these questions that should point out that his priorities and actions aren't aligned - is that getting married isn't a fairy tale.  You don't meet The ONE and live happily ever after.  To get what he seeks, he has to be serious about it and find it, and that may require him to make some changes and compromises along the way.  [/quote]

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