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Handle This: Your Luggage Gets Lost

DearSugar — Thu, 06 Nov 2008 08:00:00 -0800

You've been with your boyfriend for six months and he's finally ready to introduce you to his family, who live across the country. You know how important this trip is, which is why your nerves have been running wild all week. From the way he's always described his mother, she seems overcritical and very materialistic — the complete opposite of you. In an effort to make a good first impression, you packed all of your favorite outfits, including matching handbags, shoes, and accessories — you feel completely prepared!

After landing, you head straight to baggage claim. Your boyfriend's bag comes off the conveyor belt, but yours is nowhere in sight. You panic and when the bags stop coming, you're forced to accept the fact that your suitcase is missing. You're stuck with the clothes on your back for the next four days, and all you can think of is his mother's reaction. How would you handle this?

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Handle This: He Wants to Try Anal Sex

DearSugar — Thu, 30 Oct 2008 13:00:00 -0700

On occasion, your boyfriend has mentioned that he’s really enjoyed anal sex in the past and would like to try it with you. You've always felt hesitant about the idea, and naturally brushed off his requests. Lately, however, you’ve started feeling as if he’s pressuring you into it. One night when you’re fooling around, he pulls away from you and says that he’s bored with your sex life. He thinks it’s unfair that you haven't tried anal sex with him; it would really mean a lot to him if you just tried it; just once. How would you handle this?

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Handle This: She's Getting It on in Front of You

DearSugar — Wed, 29 Oct 2008 13:00:00 -0700

You and a close friend have made a trip back to your college town to visit a mutual friend for the weekend. Since the friend you're visiting is married with kids, you both opted to stay in a hotel instead of at her house, figuring if you shared a room, it wouldn’t be too expensive.

One night you all head out for drinks and end up running into an old male friend who used to go to college with all of you. You decide to call it a night on the early side, but your other friend is ready to party. You part ways with her, and she says she’ll see you in a few hours. Back at the hotel you fall asleep, only to wake up to some strange noises coming from your friend’s bed. It takes you a moment, but it suddenly clicks that she’s in the middle of having sex two feet away from you! How would you handle this?

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Handle This: Your Friend Ruined Your Plans

DearSugar — Mon, 27 Oct 2008 10:00:00 -0700

You have a large group of girl friends from college that you still stay in touch with. You've all been talking about getting together for a reunion night, but after months of talk, no one's taken on the responsibility, so you decide to take it upon yourself. You all agree that instead of a big group dinner out, it would be more fun to make it a girls' night in. The problem is your apartment is just too small for that many people. One of your friends has a great place for groups; you ask her if she'd be willing to let you throw it there, and she agrees.

When the weekend of the party arrives, you call your friend to confirm the plans for setting up at her house. But now she tells you that it's not a good time for her, and she's not feeling well. You assure her she doesn't have to do anything, but she refuses. Now you have a 20-person party with no location. How do you handle this?

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Handle This: Your Friend With Benefits Is Seeing Someone on the Same Night

DearSugar — Thu, 23 Oct 2008 17:00:00 -0700

Although your friends warned you about a friends-with-benefits situation, you did so anyways, and so far things have been going well. The sex is satisfying and you are both very respectful of the other, or so it seems.

One night when you have plans to meet up with your special friend for a lustful night, you decide to go grab dinner and drinks with girlfriends first. You’re totally shocked when you see your guy leading another woman out of the very same restaurant. You don’t care about dating other people, but to think of him seeing her on the same night that he plans on seeing you is just too strange. How do you handle this?

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Handle This: You Hate Your Engagement Ring

DearSugar — Wed, 22 Oct 2008 12:00:00 -0700

Although you knew you and your boyfriend would be getting married in the near future, recently he surprised you with a proposal. You were thrilled, but the ring leaves something to be desired. It’s not your style and not very pretty. You were going to ask him if you could return it, but then he told you it was a family heirloom — his grandmother’s ring! Your friends say it would be too horrible to say something, but you really don’t like it! How would you handle this?

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Handle This: He's More Interested in Porn

DearSugar — Mon, 20 Oct 2008 13:00:00 -0700

In the past few months your sex life has all but dried up. You’re always trying to initiate things, and you’ve even gone so far as to buy sexy new lingerie, but nothing seems to get your boyfriend interested. When you ask him about it, he says he’s sleep deprived and stressed out.

One night you wake up and realize he’s no longer in bed. Following sounds coming from the living room, you peek in to find him masturbating to porn on his computer, when you haven't had sex in a month! How would you handle this?

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Handle This: Your Date Can't Afford to Take You Out

DearSugar — Fri, 17 Oct 2008 17:00:00 -0700

Recently you were asked out on a date by a guy who works in your building. For your first date, he takes you on a fun factory tour of a local brewery, and you guys grab slices of pizza afterward. On the next date he takes you to his favorite burrito place and then an art gallery. Most recently you guys hit up a dive bar. You love that he’s zany, and you really connect with him in a way you haven't with a guy in a long time.

But when you ask if he'll come with you to a friend's birthday party at a sit-down restaurant, he says yes but only if you pay, since he’s broke. You don't mind paying, but since you know he has a job, you can't help but wonder if he's really broke or just cheap. How would you handle this?

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Handle This: A Rude Encounter

DearSugar — Tue, 14 Oct 2008 13:00:00 -0700

On a night out with a girlfriend, you head to the local bar. When you get there, you make your way to an empty table to settle down and order some drinks. Not two minutes go by before a couple of girls come over and demand that you move because they were there first.

When you tell them that you didn’t see any glasses on the table or jackets hanging on the chairs, they get more heated. They're obviously drunk and now they’re getting up in your faces, which is making being the bigger person all the more difficult. So how would you handle this?

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Handle This: She Wants You to Be Her Maid of Honor

DearSugar — Mon, 13 Oct 2008 09:00:00 -0700

A friend you used to be really close to throughout high school and college recently reconnected with you after you'd both lost touch. You have nothing against this friend, but most of what made you friends in the first place doesn’t really exist anymore.

You have little in common, but she still pushes your friendship. You've been accommodating so far, but only to be nice. At a recent outing she lets you know how grateful she is for your friendship since she doesn’t have anyone else outside of her fiance. Then she proceeds to ask you to be her maid of honor at her wedding in eight months. You can’t imagine saying no, but you really don’t want to say yes, so how do you handle this?

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