So long story short I hung out with my friend tonight and over a couple beers and just talking about whatever we start talking about women. He then starts to tell me how he met and is talking to these two women. They seem interested in him early on and he seems interested in them to at least see what could happen but also is taking it slow and not rushing anything. Anyways one is 34, great job, takes care of herself and things going for her in life, no kids and is looking to date now and see if it could become something more. He showed me a picture and she is cute. The other woman is 39, takes care of herself and has great things in life too, has a 15 year old son and although looks are not everything she is just gorgeous and does not look 39 at all, in fact looks barely 29. He asked me what I thought about a 26 year old possibly dating and/or being in a relationship with either the 34 or 39 year old? Honestly I could not tell him a decent answer because I personally have never been in a situation like that and have always dated women who were either my age or a few years younger or older, not 8 or 13 years respectively. You often hear now-a-days 40's is the new 30's and 30's is the new 20's. My buddy is pretty mature and established in life for his age, however I know he still appreciates having guys nights out and also being a guy in his 20's, but also has been single for a while and on more then one occasion has expressed how he wants to find someone to be with. He has gone out with women are his age but nothing ever becomes of it. I would not call these women desperate or broken, however they are also looking for someone too. I figured since I get a lot of advice from the members here on bass gear and such and there is a diverse member base I would ask what people thought of my buddies situation? I know it happens and especially in Hollywood where you have people in relationships and marrying people who are 10+ or more years older (wink Hugh Hefner wink wink). Does it seem weird or wrong for my friend to be in a relationship with someone who is 34 or 39 when he is only 26? Out of the two he told me he has enjoyed talking with and getting to know the 39 year old better. The fact she has a kid does not really scare my friend, however she did ask what his thoughts were on possibly more kids and he told her someday he would like to have a family of his own. Any thoughts, advice or whatnot?