"1. he has a child  with a woman he basically was friends with benefits with (the mother and daughter live 2000 miles away), AND she recently confessed to him she wants him closer so they can be an "everyday family" .

How does he feel about this "everyday family" idea?.

"2. He barely has a job, seems to quit them on a whim, gambles, and confessed he is pulling out of his 401k just to survive the rest of this month.".

Has he had financial difficulty do to no fault of his own?  Is he looking for employment?  What kind of gambling does he do? ..

Hi Jackie,.

Welcome to the board!!!.

I'm  not sure I'd be worried about the other woman.  They had an opps.  I think it's more important to think about if he is living up to his responsibilities.  So talk to him and see what he thinks about this other woman.  Remember that if this all works out, you will be step mom.  Are you ready for that? .

I think for me I'd be more worried about the financial issues he is having.  I don't think you are wrong to be worried!!!  You've worked hard to get where you are and I wouldn't want to just let that drop.  A man's financial responsibility (or how he handles it) is high on my list of what I want in a man.  Don't get me wrong - he doesn't have to be rich, but living within his means and working at least some to keep moving forward..

I'd ask him if he is getting help on his gambling issue.  I don't think gambling is being responsible when you don't have a job.  Be watchful and don't let yourself get in too deep before you know all of the facts..

Best of luck,.

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How does he feel about this "everyday family" idea?.

He says he isn't interested at all. He says they simply have a friendly relationship (thru Match.com) for the sake their daughter....that there never was and never will be romantic feelings. I do believe him..

Has he had financial difficulty do to no fault of his own?  Is he looking for employment?  What kind of gambling does he do? .

He quit a good job he had because he got "fed up" with not being advanced quickly up the ladder....he quit without having another job lined up, has gone 2 months without a job and depleted his savings, and now 401k. Last week he got a new job, but by the second day says he wants to quit because he doesn't like it. I dont' know, he just doesn't seem to be thinking out a plan very clearly. Just quits, and THEN figures it out...not very smart.  Oh, gambling is sports betting (Legal in my state)...he spends about $50 a day ....not HORRIBLE, but it can definitely add up. Plus, not the smartest thing to do when you dont' have a job! Ugh......

Thanks for the added info ... based on that ... quitting a job after 2 days because he "didnt' like it" and gambling $50 a day while unemployed ... no way!   Toss him back into the pond.    Totally irresponsible.   There's no way I would date using Match.com a guy who would blow money like that ... meanwhile, he's taking money out of his 401k.  .

I don't have a problem with a little sports betting for fun ... no biggie ... the problem is he can't afford to do so ... but, he's doing so anyway.  What does that tell you??.

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 Are you looking to MARRY this guy, or just have sex with him? If marriage is NOT in the plans, what's it matter. But... since you seem concerned about this, I get the feeling that you're looking for more than just sex. Am I right?.

 Z..

His irresponsible behaviour about working, and his irresponsible attitude to money would send me running..

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No one is perfect, true he has gambling problems, has to take money out of his 401K to survive, not to mention his messy personal situation.  Run, girl, run before you get really attached.

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