“Should I Warn My Friend About Her Wedding?”

My best friend is getting married at the end of October and is obviously, VERY excited. She got engaged in December and by January 31st had everything planned and paid for, including her dress, the venue, reception details, DJ, etc. Then she found out she’s pregnant. Her due date is exactly one month before her wedding. This is her first child and I don’t think she realizes what having a newborn will be like, or what kind of complications might arise during the birth and following weeks. Her mom is pushing her to move the wedding date back a couple months but my friend won’t consider it. She even thinks her dress…

“I’ve Fallen for My FWB”

It’s time again for Shortcuts. For every question, I’ll give my advice in three sentences or less, because sometimes the answer to a person’s question is so obvious and the need to hear it so great, being as clear and frank as possible is simply the best way to go. Today we discuss what to do when you fall for an FWB, dating an ex’s friend, and loaning a significant other money.

“I Can’t Tell If We’re Broken Up or Not”

I’m 29 and my 40 year old boyfriend broke up with me a couple of weeks ago. To make a long story short, he misinterpreted a comment I made and in turn decided he no longer wanted to be in a relationship. Since then, we have been talking almost every day and have seen each other a couple of times. Even though he maintains that he doesn’t want to be in a relationship, when we are together it feels like we never broke up. We spent Valentine’s Day together and he said he couldn’t imagine not spending it with me, and that I make his house feel like a home. He even…

“Are All College Guys Jerks?”

I’m a sophomore in college. Over winter break four of my guy friends from high school tried to kiss me. The kicker? All four of these “men” are in relationships. Even if I’m sending some sort of subliminal “open for business” signal, it hardly seems right that they would approach even the most sultry of vixens (which I am not…) with the intention of cheating. I’m currently questioning whether I can trust any man — at least any man under 25 — to stay loyal in a relationship when I seem to serve as an overwhelming example of their willingness to stray. — Confused in College

“Am I a Scumbag?”

I started dating “Jane” about two months ago. We met on OKCupid and had a really good first date. Unfortunately, I’ve had to commute for work each week since then, but have seen her every weekend. At the start of January, “Carissa” came onto the work project that I’m traveling for. We had instant chemistry, but I fought it since she’s a coworker (and I was seeing Jane). Fast forward to end of January, and after a long night of drinking with the team, I ended up kissing Carissa in the bar at the end of the night. Things escalated rapidly from there — mostly just physical, but we carpooled to work…

“It’s Been Five Years and My Boyfriend STILL Won’t Propose!”

I’m a 27 year old female, and I’ve been with my 31 year old boyfriend for over five years now. We have made a happy and loving life together, including sharing a home, sharing our finances, being closely involved with each other’s families, and we even have two cats and a puppy together. About a year ago we started talking seriously about getting engaged within the next six months, but by the time fall rolled around, my boyfriend told me that though he loves me and wants nothing more than a future with me, he was just not ready for an engagement yet. He had some issues from his parents’ divorces, and…

“Should I Reach Out To My Ex’s Estranged Wife?”

About six and a half years ago, I broke up with my ex-boyfriend. I concluded, at the time, that he was borderline abusive and cut him out of my life. Three years ago, I moved back to the city where we had both lived, and got back in contact to clear the air in case I ever ran into him. The contact went well, we updated each other on our lives, and have had very occasional contact since. He seemed to be living the happy life that he’d always wanted, and I was glad for him. Then, nine months ago, his marriage broke up. He and his wife are in the midst…

“Why Haven’t I Met His Family?”

I’m 25 and my boyfriend is 31 and we’ve been together for eight months. He’s close with his mom and his sister, and spends a lot of time with them (he goes over to his mom’s once or twice a week to cut her grass and fix things around the house, etc.). I know that he’s told them all about me and that they keep asking to meet me, but so far he has not introduced us to each other. He’s shared some of my baking with his mom and she loved it, so several times I’ve baked cookies or cakes for him to bring her when I know he’s going to…

“I Created A Fake Boyfriend on Facebook to Make my Ex Jealous”

I’m a 39 year-old woman and I broke up with my boyfriend of three months about two weeks ago. We broke up on bad terms; I had a hunch he was cheating because he suddenly, for no reason, hid everything on his Facebook page. I told him I didn’t trust him, and he basically said that we should just be friends. I was crushed and haven’t contacted him, but I knew he was still my friend on Facebook and would see my posts. So … I decided to invent a fake boyfriend. I created a fake Facebook identity, complete with fake friends and even a fake profile picture and then basically “friended”…

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