My Rich, Older Man Wants Me to Quit My Job—Should I?

high_end_dating_september6_13QUESTION: I’ve been with my boyfriend for about two years now—he’s 17 years older than I am. He makes really good money, and he always tells me that he wants to take care of me and that I never have to worry about any­thing as long as I’m with him. Recently, he’s started hint­ing that I should quit my job, since he makes more than enough money for the both of us. I do like what I do for a liv­ing, but I also like hav­ing him to take care of me finan­cially, and I don’t want him to think that I don’t need him. Would it be stu­pid to quit my job?

CHELSEA SAYS: In one word, yes—it would be pretty stu­pid to quit your job just because your older man is telling you to, and espe­cially if you actu­ally like what you do. What exactly is stop­ping him from pack­ing up and mov­ing on tomor­row? You have no guar­an­tee that your older man—and your cash flow—will last for­ever. Until you have a ring on your fin­ger, you’re not enti­tled to any of his money.

Before you jump the gun and quit your job, you need some type of finan­cial secu­rity, which, I’m assum­ing, is one of the rea­sons you’re with a rich, older man in the first place. But, like I said, the money can stop tomor­row, and you’ll be done for. You may feel all happy and secure with him now, but your feel­ings don’t pay the bills. Money does. And even if your older man is cov­er­ing the bills today, he may not be tak­ing care of them next month. He could leave tomor­row and you’d be left with nothing.

Don’t quit unless you’re mov­ing on to some­thing bet­ter, some­thing more secure. For exam­ple, if he wants you to quit so that he can buy you your own busi­ness in your own name, then that would be a smart move. If he wants you to quit so that you can sit at home, spend his money, and be there for him when he needs you, that’s seri­ously going to change the whole dynamic of your relationship.

TRENT SAYS: Are you this older man’s girl­friend or exclu­sive sugar baby? If you’re his girl­friend, then no, I wouldn’t enter­tain the idea of quit­ting. So, because he can sup­port the two of you, he thinks it makes sense for you to quit doing some­thing you enjoy? Why would he want you to quit a job you enjoy? If he has your best inter­ests at heart, he’d want you to seek out a ful­fill­ing life, even if that means mak­ing your own money.

If, on the other hand, it’s a con­trol issue, then I can see him want­ing you to loaf around the house, bored all day, wait­ing for his glo­ri­ous return. Regard­less, there are inher­ent risks when quit­ting your job. Will he be there to sup­port you uncon­di­tion­ally for the rest of your life? This could eas­ily back­fire if he dumps you, leav­ing you with no source of income and a big employ­ment gap on your resume.

If you’re this older man’s exclu­sive sugar baby, you might need to pon­der the ques­tion a lit­tle more. A sugar baby/sugar daddy rela­tion­ship always has expec­ta­tions and bound­aries. I’ll pre­sume you were work­ing when you two got together, which, maybe he thought was a good idea at first. Maybe he wasn’t sure if it was going to last and didn’t want you being with­out a source of income. Now that the sugar daddy/sugar baby rela­tion­ship is on more solid foot­ing, maybe his want­ing you to quit work alto­gether is his not-so-subtle way of say­ing he wants to take the sugar daddy/sugar baby rela­tion­ship to the next level. If it is, I’d want to dis­cuss every­thing and know what the new bound­aries and expec­ta­tions are. Also talk about whether or not he’s going to pro­vide you with some sort of safety net should things not work out. You need to make sure you’re on the same page.

Ulti­mately, if you’re going to accom­mo­date his needs, he has to make sure he’s taken every pre­cau­tion to accom­mo­date yours.