Category Archives: Relationships

Sassy sophisticated relationship advice for real women everywhere: dating advice, love advice, and more!

Dear Wendy: “Should I Leave My Boyfriend Behind?”

Dump My BF Before College?
Dear Wendy helps a reader who is on the fence. Read More »

I am a 21-year-old college student, graduating this spring. I was recently accepted to an Ivy League institution to pursue my graduate degree, and I have never been more excited! However, I have a boyfriend of over six years, who really wants to follow me to graduate school. At first, this seemed like a great idea. I am very happy that he supports me and we have a very strong relationship. However, he does not have a lot of ambition. While I will be going for a graduate degree, he failed out of college and has not really shown any interest in going back. He is currently a cook, and would be able to get a job pretty easily if we move. He has also talked about other labor jobs or bartending. Another concern is that he has never lived anywhere but with his parents. I have been on my own for four years. I am worried that he’ll find it difficult to live away from home. On the other hand, I think it would be a great opportunity for him to move to a city where there are many more opportunities for him. Considering all of this, I am also concerned about myself. I want to be able to take advantage of this opportunity to attend an Ivy League institution to the fullest. I do love him, and I don’t want to lose him, but I am really unsure if he should come along with me, or if I should essentially leave him behind. I don’t want to have any regrets. What do you think I should do? — Off to an Ivy

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Poll: Would You Vow “To Obey” Your Hubby In Your Wedding Vows?

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Dating Amelia: Some Dating Rules I’ve Kept And A Few I’ve Ditched

This era of my Dating Amelia column (which has been a fixture on this site, off and on, for a couple of years) is not going to last long — just this one post, actually — as I am not really dating anymore. After taking a two month dating/sex sabbatical, I sort of fell back into the dating pool when I unexpectedly met someone awesome and it’s been, for lack of a better word, on ever since. But! Over the course of my sabbatical, I thought a lot about how I would approach dating once I started back up again and I consider following a few different rules that I had either never really considered before or failed at entirely. Here are five of them — two that I have kept and three that I tossed out, not because they may not be right for you, but because they weren’t right for me. Keep reading »

Girl Talk: My Date With A Porn Star

Poor Sex Etiquette
10 things that are rude to do in the sack. Read More »
Likin' It Rough
A woman tries rough sex for the first time. Read More »
What Men Want In Bed
Do these things and he'll be a happy man. Read More »

So, a male porn star walks into a bar. I’m going to call him PS for short, to keep things simple. I’ve seen PS around Chicago before; a couple years back, we ended up at the same karaoke event until 6 a.m. But we hadn’t talked much until I ran into him at the aforementioned bar, attending a fundraiser for sex workers’ rights. See, I write about sex with a focus on S&M and I do activism around it as well, so I end up coordinating with sex worker activists a lot. Plus, sex workers totally know how to put the ‘fun’ in ‘fundraiser.’

As we sipped on drinks, PS and I chatted about sex education, work/life distinctions, and that sex toy demonstration at Northwestern that landed a professor in the center of a controversy. Keep reading »

Dear Wendy Updates: “Doesn’t Use Pot Holders” Responds

Dating Good Guys
boyfriend photo
Not every woman wants to date an a-hole. Read More »
How To Be Romantic...
...without being creepy! Read More »
Dater X
dating photo
Ten things Dater X did right as a single girl. Read More »

It’s time again for “Dear Wendy Updates,” a feature where people I’ve given advice to in the past let us know whether they followed the advice and how they’re doing today. After the jump, we hear from “Doesn’t Use Pot Holders,” who wrote in because her boyfriend’s sister, whom he shared an apartment with, hated her. After the jump, find out if the sister managed to wreck the relationship and how everyone is doing today. Keep reading »

He Said/She Said: Our First Vacation Together

This love train continues to steamroll ahead, flattening my former single girl life in its path and chugging into serious couple territory. After only a month of living together, a few pre-planned events came to fruition all in the same week – getting our puppy, meeting his parents and escaping to the beach for our own spring break. Keep reading »

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