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You're paying for his groceries and helping him with rent? He's definitely using you. It sounds like he doesn't even want to be friends, he just wants a roommate who pays for more than half the expenses. Also very rude he told you that he told his friends his not even sad. Are both names on the lease? Can one of you move out? Find a new roommate if needed.
Also for future reference, if your needs aren't being met in a relationship, instead of “show me you love me”, you need to be more specific about what you want. For example: “Hey it would really mean a lot to me if we could plan a date night once a week.” No 20-something guy is going to want to sign up for a guessing game to try to win your love. If you want something reasonable and specific, just ask.
this is all such creepy advice. against the wife’s wishes, drive her there then try to get in and if refused, sit at the hotel until she’s done. is the goal here to ruin her reputation at work with this controlling advice?
I don’t think she’s unfaithful or wanting to go through a “hoe phase.” I think she wants you to make your own friends and discover life outside of her and you’re talking her out of it repeatedly.
Nothing about this points to her wanting to fuck other people, she’s probably identifying signs of codependency that don’t mesh well with your lack of desire to marry. She sees you have different needs and wants and is actively encouraging you to find some new friends so you’re not alone when she moves on. Take the advice.
You can choose to believe this is about a “hoe phase” if you want but you’re the only one that will suffer if you do.