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Ask MISTER Carl: "My Boyfriend Is Cheating...Maybe? Help!"

02/21/2014 10:38 am ET | Updated Feb 02, 2016

Welcome to "Ask Mister Carl." I'm Carl Sandler, the founder of the gay mobile app, MISTER. You can also find me on SiriusXM Radio OutQ's The Morning Jolt discussing gay dating and relationships. In this series, I invite readers to share challenges that they encounter in their dating and love lives. Remember, there are many ways to look at every issue. If you disagree with something I write, be positive and share your own strategies or suggestions in the comments.

Dear Mr. Carl,

I'm a sophomore in college in a committed relationship with another guy here on campus, and I've got a serious case of Relationship Jitters 101. My boyfriend likes to go out and party, while I'm more of a homebody who'd rather spend a nice, not-so-boozy night in with friends. I've found myself getting anxious when he goes out, because I'm afraid he might go home with another dude after a night out of living it up. He assures me I have nothing to worry about and that he's always on his best behavior, but my last boyfriend cheated on me left and right, so I'm a little gun shy about getting burned again. Any advice on how I can get over my insecurity?

-- Sophomore in a Slump

We all bring some baggage with us when we embark on a new relationship, and yours appears to be as hefty as a Louis Vuitton steamer trunk (with an equally exorbitant emotional price tag attached). It's time to start unloading those bags and stop projecting before your boyfriend starts packing his.

You've already taken a great first step, which is openly and honestly sharing your concerns with him. After all, trust is the basis of all relationships, and learning how and when to trust a partner is a skill we all need to practice and hone. Now it's time to let it go -- to a point. I'm not saying you shouldn't trust your hard-partying, boozing, college sophomore boyfriend's claims of monogamy. What I am saying is that he's a hard-partying, boozing, college sophomore. Even with the best of intentions, the chances of him slipping up at some point are as about as high as a freshman taking his first hit off a gravity bong. So to protect yourself physically, you two should be sure to practice safe sex, at least until you feel more certain about his fidelity.

Whether your fears ultimately turn out to be true or not, learning to deal with your trust issues and the fallout from your previous relationship -- preferably with the help of a professional -- is crucial. With any luck, you'll learn to overcome (or at least manage) your insecurities with men in a healthy, positive way. Or, maybe you'll realize you need to pick a different type of partner. The good news is that you're young, and the more work you do to address these issues now, the better off you'll be in the long run. Keep those bags close. You've got plenty of relationship road still to travel.

Dear MR. Carl,

At what age is a man too old to wear a Miley Cyrus t-shirt? Or a Abercrombie & Fitch polo shirt? Or a backwards baseball cap? My 43-year-old boyfriend regularly wears all of these age-inappropriate items of clothing and more. When we first met nearly a decade ago, he had this preppy style that I found so handsome on him. But ever since he turned 40, he suddenly started shopping at "hipster" stores like American Apparel and Urban Outfitters. Frankly, I'm sometimes embarrassed when we go out because it seems like his clothing choices are such a desperate attempt on his part to look younger. Is there some way I convince him to stop chasing the sartorial dragon, embrace his age and get my preppy prince back?

-- Closet Case

As a 42-year-old owner of a pair of camouflage Air Jordan high tops and someone who's worn a "fitted" Yankees cap with a suit to a black-tie wedding, I'm probably the last person you should be asking for advice on this particular question. Are some of my wardrobe choices too "young" for me? I suppose some of them might be. But the way I look at it, my occasional affairs with age-inappropriate attire is something that makes me, well, me.

Your embarrassment over your boyfriend's clothing choices tells me there are probably deeper, more complex issues at play here. And like most complex issues, the only way to deal with them is to own your discomfort and find a loving, honest and real way to share what is going on with your boyfriend. But before you start telling him how you feel, give him an opportunity to talk about what prompted his change in style. Let him tell you his own story about his new fashion choices. Ask him questions rather than making up stories. Then share with him how it makes you uncomfortable and own your discomfort. Remember, another person might actually view his new fashion as bringing sexy back. This is your issue as much as it is his.

Sadly, I can't click my Jimmy Choos three times and make your boyfriend magically change back into a preppy prince. Leather paddles were sold out at Mr-s-leather.com too, so beating some fashion sense into him is also not a viable option. Sigh. The author Dan Savage wisely talks about the "price of admission" in relationships; those things about your BF that you can't change and need to learn to accept in order to be in a relationship. If, after a decade-long experiment in intimacy, your price of admission is a Miley Cyrus t-shirt and a backwards baseball cap, that's what us Jersey girls call, a bah-gain.

Have a question for me? Send it to AskMrCarl@misterapp.com