Ask Chelsea

How Do I Respond to My Sugar Daddy’s Naughty Texts?

QUESTION: My boyfriend sends me naughty mes­sages all the time (texts and pic­tures). I usu­ally just send back a happy face because I don’t know how else to respond. I know he prob­a­bly expects some­thing naughty back, but I’ve just never known how to respond. Help! CHELSEA SAYS: Assum­ing you and your boyfriend are already sleep­ing together, a lit­tle mobile lov­ing is per­fectly accept­able. For your mes­sages, keep it sim­ple and have fun with […]

How Do I Ask My Sugar Daddy for Something That’s More Expensive Than He Usually Spends on Me?

QUESTION: The other day I saw a really expen­sive designer hand­bag that I absolutely fell in love with. My sugar daddy usu­ally has no prob­lem spend­ing money on expen­sive gifts for me, but this bag costs a lot more than he usu­ally spends. How do I ask him for it with­out com­ing off as being a spoiled brat? CHELSEA SAYS: There are a few ways to go about this with your sugar daddy. […]

How Do I Get My Older Man to Dye His White Hair Without Offending Him?

QUESTION: Last year I mar­ried my boyfriend, who’s about 19 year older than me. He’s just started sport­ing white hair and when I sug­gested he tries dying it, he totally freaked out on me. I think he’s incred­i­bly attrac­tive, espe­cially for an older man, but I think he would look even bet­ter if he cov­ered up the grays. How do I bring it up again with­out mak­ing him angry? CHELSEA SAYS: I don’t blame […]

I Hate My Sugar Daddy’s Gifts—How Do I Get What I Really Want?

QUESTION: My sugar daddy always buys me expen­sive gifts, but he has really bad taste, so I never really like what he picks out. How do I get him to buy me stuff that I would actu­ally like? CHELSEA SAYS: You obvi­ously need to get a lit­tle bet­ter at drop­ping hints around your sugar daddy. He’s prob­a­bly not giv­ing you what you want because he has no idea what you want. When you see […]