Sex & Relationships

Ask Sharleen: Your Dating Conundrums Solved!

Opera singer Sharleen Joynt—our always on-point Bachelor recapper, season 18 contestant and all-round cool girl—addresses your most pressing matters of the heart in her debut column. This month: the lowdown on dating rich and ditching the friend zone


Can two kids from different backgrounds make it work? (Photo: Rex USA)

Silver Spoon Doom
I’m currently in a relationship with someone from a higher socio-economic class. All of my previous partners had been raised in lower-middle-class, blue-collar homes—just like I was—which never really occurred to me until I starting dating my current partner, whose parents are well-off academics. Our different upbringings have been a constant source of tension. We communicate well enough, but things become cloudy whenever the subject approaches money. This relationship is probably beyond mending (he’s also moody and picks fights with me whenever he’s stressed at work), but I’m anxious about the future. What if, down the road, I meet someone great who also happens to be from money? I don’t want to discriminate, but my current situation has left me wary of dating rich guys.

Sharleen: Your predicament is tough; there’s no denying that in dating, it helps to have similar backgrounds. Before I get to what I think the problem is, be sure to ask yourself whether you’re casting any quiet judgments. I once dated someone from an affluent upbringing who endured judgment almost every day. His recounting of a cool experience or expressing excitement about a recent purchase came off to others as boastful, which wasn’t his intention at all. There’s a difference between a person who is privileged yet good-hearted, and one who’s privileged and entitled. Ask yourself if there is any judgment—from either party—about how money is valued, shared or spent. You seem open-minded and communicative, so I’m sure this isn’t an issue, but allow yourself a little introspection to ensure there’s no bitterness or insecurity on your part.

For better or for worse, I suspect the discrepancy in your upbringings is not actually the cause of strife in your relationship. Yes, the world of finances can be a minefield but, money aside, do your personal values align? Do you see eye to eye on the roles you each play in the relationship? Do you agree on things like morals, religion, marriage, sex and kids? The most important asset in any relationship is compatibility. You can come from different cultures, different classes—and even speak different languages!—while still being compatible. Yes, meeting someone who was raised very similarly to you can equate to higher compatibility, but money and social rank don’t have as much of an effect on a grown person’s values as one might think.

Only you and your partner know if this particular relationship is past the point of mending. For what it’s worth, I think your “constant source of tension” is about the two of you in the present, not your disparate pasts. Regardless of what happens, toss your anxiety and keep an open mind. What you’re looking for exists, and your partner’s upbringing should only enhance your relationship, not hinder it.

Just Friends Forever
I am the girl who always ends up being the “best friend” of whatever guy I have strong feelings for. I enjoy these friendships, but I’m getting tired of the one-sidedness. I always give too much of my emotional self, and then the guy often turns around and finds the girl he’s “gonna marry.” Guys always tell me how great I am, but that’s hard to believe when they never want to date me. How can I break this cycle?

Sharleen: I’m a firm believer in equality and reciprocation. It might seem harsh, especially if you really like a guy, but resist always being there for someone who doesn’t show you that same courtesy.

As old-school as this sounds, there is no “winning over” men (not romantically, anyway). If you’re interested in a guy, your time, emotional support and perseverance are not the traits that will make him realize what a catch you are. Rather, think chemistry, intrigue, easy compatibility and the fun you have together.

My advice? Only carve out as much time for him as he does for you (this includes texting), and instead of being tirelessly supportive, just be your unique, interesting, sparkly self. Have hobbies and an active social life. Keep busy. Be sure to pay attention to his signals, good or bad, and don’t waste your time on someone who doesn’t make you a priority.

Down the road, in the right relationship, you can give as much of your emotional self as you desire. Do be caring and supportive—when your man has earned it. But until then, your time and energy are valuable. Don’t give them away so freely.

Have a question for Sharleen? Email your queries to with Ask Sharleen in the subject, tweet us @FLAREfashion or post on our Facebook page using #AskSharleen. Then, look for her reply in our August issue!