Category Archives: Relationships

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

This Blind Date Was More Awkward Than Yours

Reasons To Blind Date
blind date photo
Ten reasons you should consider going out on a blind date. Read More »

Blind dates are awkward for everyone. There’s enough to worry about without discovering that your date just so happens to be your long, lost sibling. Um … yeah. Try recovering from that awks moment. And here I was thinking I had had the most awkward blind date of all time. He told me he was under investigation by the FBI during our first drink. Keep reading »

Girl Talk: I Want The Job And The Guy After I Graduate

This month, I turned 22. Young, I know, but for me the birthday served as another float in the parade of reality that my graduation day is marching closer with each passing moment. Instead of the usual array of fun and frivolous gifts wrapped in brightly colored paper, far too many people chose to get me “work clothes” for my birthday this year.

I am graduating from New York University in May. And it’s not just others who are preparing me for the life change that’s about to happen. Each morning, I wake up and remind myself that I need to get a job—and not of the smoothie shop variety. I’ve spent more time than I care to admit contemplating how to craft the perfect employer-alluring business card and website. And if all this worrying, wondering and work wardrobing wasn’t enough, almost every conversation I have had with someone 25+ over the past five months has turned into a mental probing of my potential to deal with “the future.” Keep reading »

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?

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 »

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