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Dear Dategirl,I am a 41-year-old woman and have been trying to get
Dear Dategirl,I am a 41-year-old woman and have been trying to get pregnant with my gay best friend.…
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Dear Dategirl,My husband is a professor, and as such is consistently surrounded
Dear Dategirl,My husband is a professor, and as such is consistently surrounded by beautiful young girls. This never…
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It Really Is the Thought That Counts
Dear Dategirl, Up until this Christmas, I really liked my girlfriend. We’re both 23, but she’s in college…
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Holiday Blues
Dear Dategirl, By the time you get this, I’ll have wasted another holiday with my in-laws. I’ll have…
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All I Want for Xmas Is a Roll in the Manger
Dear Dategirl, My boyfriend of almost one year is fucking amazing. He’s affectionate, sensitive, manly, emotionally present, vulnerable,…
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Cuckolded or Koo-Koo?
Dear Dategirl, My partner has had some inappropriate interactions with members of the opposite sex. I’ve discovered the…
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Crabby Cougar Seeks Randy Cub
Dear Dategirl, While I cringe at the whole “cougar” thing, I am increasingly interested in finding a younger…
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Should I Marry Someone I Don’t Love?
Dear Dategirl, I’m not in love with the man I’m going to marry. He loves me. He’s in…
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Is the Missionary Position Out of Style?
Dear Dategirl, I haven’t had sex in the missionary position for at least a year. That’s not for…
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Better Late Than Never?
Dear Dategirl, My best friend in high school was a girl I always liked, but never made a…
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Beejs and Backsies
Dear Dategirl, How can I convince my boyfriend to go down on me? He thinks it’s gross. In…
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Same-Sex Bitchy Ex
Dear Dategirl, Here is the situation: I dated a girl for a few months. It was complicated, as…
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What About Two Lips on an Organ?
Dear Dategirl, Tonight my friend Lola’s ex told her that if a guy comes on your chest, he…
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When Your Friend Loves a Leghumper
Dear Dategirl, Last night I ran into a good friend of mine and her somewhat-new boyfriend at a…
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How to Say “You’re a Tragic Lay”
Dear Dategirl, I recently hooked up with a hot guy who’s obviously never been told—by any of the…
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Get the 411, Hon
Dear Dategirl, One of my closest friends is about 10 years older than I (so she’s in her…
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Awkward With Asperger’s
Hello, Dategirl, While I don’t feel it truly defines me, I have Asperger’s. There are many stereotypes about…
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A Tale of Two Husbands
Dear Dategirl, Just found out that my husband signed up for ashleymadison.com. He has cheated in the past,…
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Dating Dorks
Dear Dategirl, So I made out with a friend on vacation. It was weird, because he is your…
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Social-Media Mismanagement
Dear Dategirl, I need your opinion. Last night my man and I had an argument, and this morning…