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99 Problems: Tyra Banks Says Let Your Grandma Help You Date

The supermodel and host of America's Next Top Model is here to advise you on how to deal with matchmaking seniors, dress thieves, and boyfriends who flirt with dudes.

Do you have a question for our fabulous advice columnists? Send early and often to [email protected] and look for their answers right here.

My grandma moved into a retirement complex a few months back. I go visit her every few weeks to take her out to Olive Garden — it’s a long-standing tradition, and her absolute favorite restaurant. Lately though she’s been bringing different friends with her to lunch, and more awkwardly, their grandsons come along too. She’s clearly trying to matchmake, and I don’t know how to tell her she’s got terrible taste in guys. Help!?

Being a single girl myself, I know what you're talking about, girl — the dreaded set-up. As awkward as this situation can be, you know the ol' saying that you have to kiss a lot of frogs to find a prince? What if you told GramGram that you don't want any more boys sharing your endless salad bowl and missed out on someone incredible? You never know, the next dude could be your soul mate, your best friend, or just someone with an interesting story to tell. Plus, your grandma wants to feel like she's helping you. I say give her a hug and a wink, tell her you know what she's up to, and you appreciate it. Then give her a few hints about what kind of guy floats your boat so she can narrow in on the search.

A lot of my college friends are really wealthy. They all spent their summers on luxury yachts and/or in five-star beachfront hotels. (They’re Rich Kids of Instagram, basically, but I still like them.) In a moment of weakness, I lied about my summer plans and said I had glamorous vacations lined up too. I don’t know why; the reality is I’ve been waitressing back in the Midwest. How do I deal with this once we’re all back on campus? I don’t want to keep lying but I’m worried the whole “money issue” will be really awkward if I come clean?

Congratulations, you're human! Insecurity can cause all kinds of shady instincts to surface. Next time you feel wack, own it, don't hide it. Something like "I'm sure it was nice to eat pizza in Italy but I was chillin' at Sbarro in the mall and collecting a paycheck, aren't you jelly?" You know, the best thing about Instagram is the filters (I am addicted). Life is a lot like that, too. You get to choose what filter you put on your story. You can tell your friends when you get back to school that things didn't work out the way you thought they were going to, but it's okay, you ended up having a great summer, anyway. It ain't all about the money, honey.

Every summer my boyfriend and his folks spend a month at their beach house in Greece. He called me last week admitting he’d gotten really drunk one night while out at a gay bar with his brother (who's gay) and started flirting with other guys — just for his self-esteem’s sake, he claimed, and it didn’t go anywhere. I think I believe him, but still, I’m upset. He doesn’t think it’s a big deal, particularly because he owned up. Am I overreacting?

Wow. That's a tough one. I'm trying to put myself in his shoes. I haven't ever flirted with girls to feel better about myself. Have you? Is that a thing these days? On one hand, I applaud his honesty in sharing this with you. On the other hand, once he's back in the states I think you two should have a serious heart to heart. Did you know that studies show men reveal more in conversation when you're not looking at them, interrogation-style? So pick an activity that he likes — play video games, go golfing, have him drive you on a road trip — anything to give his eyes focus elsewhere so that he doesn't feel directly confronted. Then ask him some hard questions in a loving, accepting tone. Does he fantasize about men? Has he ever Googled gay porn? How did flirting with men make him feel? Would he like to do it again? Does he think he's bisexual? I don't know what the outcome will be for you two, but I think some honest discussion should be had, with the intention of making sure you're both in the right relationship. Good luck!

Since January I’ve lost just over 50 pounds — I made a New Year’s resolution to get healthy and somehow kept to it. I feel great, and though I’m not quite “a whole new person” I do feel like I have a better attitude and outlook on life. So why don’t my friends and family seem to see it that way, and how can I make them 1) stop acting like bitches and 2) support me as I try to stay in this happy place?

Weight loss always seems to bring up unexpected emotions — not just for yourself, but for the people you're close with. When you make a drastic change in your life, in spite of the fact that you're making a strong and healthy move, your loved ones can feel judged and scared. Now that you're not eating cake, do you think they shouldn't eat cake? Why can't they lose weight like you did? Will you want to find new friends now that you're smokin' hot? Will you still want to hang out and eat greasy food with them on Friday nights, or will you become a gym rat and only drink tofu smoothies? I suggest that you address their attitude openly — ha, "stop acting like bitches" might not the best way to go about it. Let them know that you're happy with your new approach to health, but it doesn't mean that you're not happy with them, and that you guys can still have a meaningful relationship, it's just going to shift a bit now that you're not engaged in all-you-can–eat Oreo contests. Tell them that you'd love to include them in some of your new activities – a sunny hike, perhaps? But if they're determined to sit on their butts, you'll still come sit on your butt with them. With your tofu smoothie, of course.

My three brothers and I each just received a large inheritance. My parents and our extended family are pressuring us into each making a donation to our church. I still attend services when I’m back home just to be polite, but I don’t agree with the place’s stance on a lot of social issues — flyers supporting Chick-fil-A were handed out one Sunday just recently, for example. I wouldn't feel comfortable emboldening those attitudes financially, or, you know, at all, but I don’t think my folks will understand. What can I do?

I have always loved receiving advice from my family — my mother actually used to be my manager when I was starting out as a model. That doesn't mean we always agree, it means that we always respect each other's right to have our own opinions. It sounds to me like attending church services when you're visiting your hometown is a lovely gesture to make, even though you've decided that your family's church doesn't reflect your personal views now that you're an adult. But investing money in something that you don't believe in is another story. The next time they bring it up with you, please tell them that your plans for your inheritance are personal and you'd prefer not to talk about it. If they insist and push, tell them that you don't feel comfortable supporting a business that doesn't fall in line with your own beliefs of acceptance and equal rights for all. If that's how you feel, I hope that they'll respect your decision. Religion is, after all, about love and forgiveness, right?

I lent my roommate a designer dress a few months back for a wedding she had to attend back on the West Coast. She claimed she left if there by mistake, but she just got tagged in a bunch of photos from another formal event she went to here in New York last weekend while I was out of town... yes, she’s wearing the dress. Can I go rifle through her closets to take the dress back? What if she gets mad about me “invading her privacy” if I do?

Dang, roommates be crazy! Pull up the photos and show her your proof. Busted! Get your dress back. Then get a lock for your bedroom door.

Follow Tyra on Twitter @tyrabanks and catch America's Next Top Model Cycle 19: College Edition Fridays on the CW at 8 p.m. EDT!

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