“How Can I Tell My Roommate I Know He’s Gay?”

“Matt” and I met the first week of college and have been close ever since. Over the last ten years, we’ve seen each other through a family crisis or two, break ups, unemployment…the list goes on. We have so many wonderful memories and I love him dearly. We’ve been living together the last three months and — other than typical roommate issues — everything is going well. Yesterday, I had lunch with another old friend. She used to be very close to Matt (they dated briefly a million years ago), but they have been growing apart for a while. During our conversation yesterday, she dropped a huge bomb. Five years ago, Matt…

“My Boyfriend’s Brother Died. How Can I Be Supportive?”

New readers, welcome to Dear Wendy, a relationship advice blog. Read some of the most popular Dear Wendy posts here. If you don’t find the info you need in this column, please visit the Dear Wendy archives or the forums (you can even start your own thread), do a search in the search bar, or submit a question for advice at wendy(AT)dearwendy.com. About a month and a half ago, I started dating a really great guy. We have incredible chemistry and a lot in common. However, our relationship has already hit a huge hurdle: two weeks ago, his brother passed away very suddenly. Adding to that pain is the fact that his…

“Gross! My Boyfriend Smells Like Olives!!”

Dear Miles, My boyfriend smells like olives. Recently, he took me to dinner at a very romantic tapas bar and we were having a nice time. Until I accidentally ordered a dish that has olives (Eeeewwww.) “No big deal” he said. He LOVES olives and traded plates with me. But, of course, that night when we kissed all I could taste were those gross olives. Even weeks later it’s all I can smell whenever he gets close. I finally talked to him about it and he swears he hasn’t been eating any. I think I hurt his feelings. Nevertheless, he still smells like olives. — In a Pickle.

“Why am I Such an Idiot??”

Dear Miles, I dated this guy at work (Never again!) and don’t know how to handle him. I have a strict policy about not dating co-workers and don’t know why I broke it for him (I’ll call him Larry.) I wasn’t even that into Larry but he asked me out and, before my mind could say no, my big stupid mouth said yes. Needless to say, the date was boring, we both had too much to drink and then I let him kiss me (I don’t know why I did that either.) When I arrived at work Monday morning he mentioned a wedding we’re going to in a couple weeks. I sort…

“How Can I Get My Money Back From My SIL?”

Dear Miles, My sister in-law and I usually get along pretty well. That is until we had lunch a few months back and she asked to borrow $700. She claimed her job was late with their paychecks and assured me she’d pay me back as soon as she got paid. She also asked me not to tell my husband (her brother.) I’ve seen her at a couple of family gatherings since then and she acted like none of this ever happened. And when I attempted to bring it up she changed the subject. Should I say something to my husband? (We haven’t been getting along well lately and I don’t want to…

“Am I a Selfish Bride?”

I got married exactly one year ago to my now-husband. We decided to get hitched at City Hall and because he’s foreign, the whole thing was organized very quickly, with both our families flying to the west coast on a week’s notice, from different countries. We sent out a last minute email to our very large group of good friends saying that we were getting hitched at the courthouse but we were having a reception that night. The whole thing was very informal (just like we wanted it) and all our friends came and we all had a great time. The problem is, only two of our friends got us wedding gifts….

His Take: “Will He Ever Quit Drinking So Much And Settle Down?”

I love my boyfriend very much, but he’s a restless soul and loves to go out at night as much as possible. I totally trust him and what’s going on, but it happens so frequently during the week (3-4 days a week, while he holds down a demanding job), and he ends up drinking what I think is way too much (4-5 beers per night). If we were in our 20s, I would care much less. But we are both in our 30s, and this is the phase of my life that I’m looking for a life partner and potential father of my children. Granted, he spends a good amount of quality…

“How Do I Get a Commitment-Phobe to Commit?”

After two bad break-ups and a year off from relationships, I finally decided to give it a try with this new guy, David. He’d never had a girlfriend before, and said he said he didn’t want to just hook up, but wanted a relationship, which was great news for me, as I felt like I’d finally met someone I was willing to put my heart on the line for. Because he holds an executive position in our student government and is taking four classes, we didn’t get to see much of each other, but I was fine with that. Then, after not quite a month, he blindsided me with a break up….

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