Category Archives: Relationships

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

Dear Wendy: “I Think I’m In Love With My Best Friend”

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 falling for your best friend, breaking up with frenemies, and when to butt out and stop giving advice. Keep reading »

Dear Wendy Updates: “Second Thoughts” Responds

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 “Second Thoughts” who was planning to have her boyfriend move with her next year when she starts college but worried he was too immature to be a good long-term partner. Has she decided to move without him? Has he convinced her he’ll grow up? Find out all after the jump. Keep reading »

Girl Talk: My Nerdy Flirting

I recently had a flirtation with a guy whereby we debated the merits of using Dictionary.com versus the actual hard copy, old school, book version of the dictionary. And I realized, with some degree of alarm, that this felt familiar. That this—this courting by way of words—was not a one-time thing. It was a recurring thing. It was my thing. Keep reading »

Can You Tell How A First Date Is Going To Go In The First 3 Seconds?

How long does it take to make a first impression? 15 seconds? 7 seconds? 3 seconds? I’ve been doing some dating lately (FOR THE LOVE OF GOD, SOMEONE HELP ME), and I’ve come to the conclusion that I can tell how a date is going to go within the first three seconds. My shrink thinks this is poppycock, some fantasy of omnipotence, but what does he know? In any case, I believe — and this is the key — that if I’m totally honest with myself, I know exactly how the date will go virtually immediately: the second I set eyes on the guy.

When you go on a first date, is your first impression usually right or wrong? Keep reading »

Dear Wendy: “Should My New Boyfriend Get My Parents A Christmas Gift?”

My boyfriend asked me last night if we/he should get my parents and sister each a gift for Christmas. This is our first Christmas as a couple and the first serious boyfriend I had around the holidays. He has already met my parents and sister and they all like each other. Should he get them a gift? Should I tell my family that they all need to get him something too? So far I told him I’d let him know but I’m really not sure what the best thing to do is. — First Christmas Together

Keep reading »

How To Go To A Party Alone

It’s holiday time again, which for me means lots of parties to go to … solo. My first instinct is usually to try to snag a pal to bring with me to party crash, but recently, I was invited to a party where the host explicitly instructed guests not to bring a plus one. I was dreading showing up there, thinking it would be uncomfortable, but once I arrived, I embraced it and ended up having a great time. After I deftly extricated myself from a dull conversation with an awkward woman with a neck twitch, I hit it off with a group of dudes with nerdy glasses who shared my love of stupid dance moves. Needless to say, I have a new appreciation for going to parties alone. After the jump, some tips for making the best of a stag situation. Add your suggestions in the comments. Keep reading »

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