Category Archives: Relationships

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

The Soapbox: This Might Sound Crazy, But Let’s Bring Back Good Manners In Dating

I-Banker Email
Rejected i-banker "Mike" penned a 1,615-word email of woe. Read More »
Dating Don't
Thou shalt not "ghost" the person thy does not want to date. Read More »
Dating Don'ts
How NOT to act crazy when online dating. Read More »
Dating Don'ts
How NOT to date a coworker. Read More »

Over the summer, I had a first date with an attractive, smart guy who emailed me over an online dating site. C— was Harvard-educated, a lawyer, and a dead ringer for the actor Terrance Howard (i.e. super hot). We had a lovely conversation and was a total gentleman until the end of the date: he paid for our drinks, walked me to the train, and kissed me on the lips before telling me he wanted to see me again soon.

I texted him the next day to say “thank you for drinks!” I never heard back. Not a single peep. I got “ghosted.”

Well, I never heard back for three months, anyway. One afternoon, I randomly received this text message from C—:

Hey Jess, it’s C—. I don’t have a great excuse for why I fell off the planet. I got really busy and things got messy with an ex that I didn’t want to be bothered with while pursuing something new. If you are still interested, I’d like to see you. Keep reading »

Dear Wendy: “Should I Give Up My Prestigious School For My Boyfriend?”

LDR Tips
Seven questions to ask before you start a long distance relationship. Read More »
Pin-Up Dreams
Dear Wendy: "I'm Jealous Of Calendar Girls" Read More »
Dear Wendy
"My fianc Read More »

Guest columnists and contributors are generously sharing their talents and insights while Wendy is taking some time to care for my new baby. Today’s letter is answered by prolific Dear Wendy commenter and social media consultant, Sarah Huffman.

My year-long relationship recently went long distance. I had gotten into several master’s programs — a few decent ones near him and an amazing one far away — and because of future career potential and pressure from everyone (including him) I chose the more prestigious, far-away program. The problem is that I am completely miserable. I am so in love with my boyfriend and I miss him so much, I don’t know what to do with myself. My school is a lot of work, which adds to the stress level. My fellow classmates go out and have fun – I’d rather get more work done so that I can have a few days to visit the boyfriend. Keep reading »

Girl Talk: Pooping Is A Feminist Issue

My Picking Problem
How I gave myself a bald spot and other stories of life with dermatillomania. Read More »
Period Love
If you love me, you'd better learn to love my period. Read More »

Mary and I were sitting on her couch, laughing. “But wait, no seriously, is pooping a  feminist issue? Why aren’t we talking about this?” I asked.

It was funny, if only because there was some truth in the (often female) phenomenon of “holding it in.” There’s this prevalent idea that girls don’t poop.

“Ugh. I hate that part of dating,” Mary said. “ I can remember holding it in all weekend, waiting until we got to a restaurant or somewhere!”

I knew this move all too well. I wondered, Is this every woman’s secret? Keep reading »

A 1,615 Word Example Of How Not To Get A Second Date

The Rudest Email Ever?
In defense of the woman who sent a rude email to her future daughter-in-law. Read More »
Technology And Dating
Technology and dating dos and don'ts. Read More »
Stupidest Emails
The stupidest things guys have said via email. Read More »

Some of us may be feeling sorry for ourselves that we’re single this holiday season. But it could be worse! We could be getting a 1,615 word missive from a guy we went on one date with, chiding us for leading him on by playing with our hair too much and making eye contact. Such is the case for Lauren, who received a lengthy email from Mike — an investment banker who makes “real money, not Monopoly money” — in which he expresses his disappointment in her for not wanting to go on a second date. After the jump, you’ll find his unedited manifesto, which is making the rounds on the internet. Please read it in its entirety. To be honest, it’s hard to tell if Mike is suffering from some very real issues and, if so, what they are; some have suggested that Mike “obviously” is on the autism spectrum and therefore this email is not to be laughed at, while others think he is simply a Wall Street douchebag with a serious entitlement complex. Perhaps he is all of the above? Anyway, read on and discuss. [Observer]

Keep reading »

Girl Talk: I’m In Couples Therapy

Therapy Boundaries
How much should you know about your psychologist's personal life? Read More »
My Picking Problem
How I gave myself a bald spot and other stories of life with dermatillomania. Read More »
Depression Overshare?
depression photo
Should Jessica not have told her boyfriend's parents she's depressed? Read More »

A few months ago my fiancée and I watched an episode of “Thirtysomethings” when Elliot and Nancy start seeing a marriage counselor. At first they are both embarrassed and ashamed, and neither wants their circle of friends to know. But as it goes in a television show, the secret gets out and they both feel like crap.

Call me a stereotypical New Yorker, but I love therapy and never understood why people are embarrassed or ashamed about it. I also never got why people wait until they feel like breaking up to start couples’ therapy. Therapy got me through adolescence, depression, disorder, and my relationship with my fiancée. Keep reading »

Girl Talk: I Was The Ugly Friend

My Picking Problem
How I gave myself a bald spot and other stories of life with dermatillomania. Read More »
I'm Not Beautiful
But that's okay. Read More »
Tell Me I'm Pretty
Is it so much to ask to want to be told I'm beautiful? Read More »

When I was young, my parents told me I was beautiful and I believed them. I went out into the world feeling confident about my womanly charms and things went smoothly for me. I always managed to find a boy who would tell me I was perfect, even if he did wear suspenders and a really old T-shirt that said “STATISTICS means never having to say you’re certain.” And then I moved to Manhattan when I was 22, and everything changed. Keep reading »

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