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Dating Tips

Advice for dating, first impressions, and getting to know someone new.

What to Do When He Brings a Friend Along on Your Second Date

October 9, 2026 by Olivia Parker
Woman at a brewery trivia night on a second date with two men at the table

My friend Priya texted me from a Denver brewery one snowy Thursday in March. It was 7:35 at night, and her second date had just begun. Cole had walked in for trivia night with his buddy Marcus right behind him. He grinned and said “Marcus was bored, so I brought him” to her. Priya had … Read more

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What to Do When He Plans a Really Expensive First Date

October 9, 2026 by Olivia Parker
Couple at a fancy steakhouse table during an expensive first date

A reader named Jenna wrote to me at 1:15 in the morning one hot July night. She had just come home from a first date in Atlanta. Derek had picked a fancy steakhouse in Buckhead for 8 that evening. He ordered a $190 bottle of wine before she even sat down. The final bill was … Read more

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Signs You Are Settling for Convenient Instead of Right

October 6, 2026 by Olivia Parker

My friend Sana almost moved in with a guy named Derek last year. It was a Thursday night in late October, around 9pm. Derek lived twelve minutes from her office, which mattered more than it should. He handed her a spare key and said it just made sense. Sana told me she nodded, though something … Read more

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Signs He Is Emotionally Available on a First Date

October 4, 2026 by Olivia Parker
Couple smiling and enjoying coffee together on a first date at a cafe

I met Jake at a bookstore cafe at 6:15 on a Tuesday. I ordered plain black coffee and my hands were shaking a little. He asked what I was reading before he even sat down fully. That one question told me more than his profile pictures ever did. Three years and one closed distance later, … Read more

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What to Do When He Asks to Facetime Before Your First Date

October 2, 2026 by Olivia Parker
Woman on a video call on her phone before a first date

I was sitting on my childhood bed on a Thursday at 9:15 at night. It was late summer and I was home from college for only two weeks. My phone buzzed with a message asking if we could video call first. We had talked for a month online but never once seen each other live. … Read more

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How to Spot Love Bombing on an Amazing First Date

October 9, 2026September 30, 2026 by Olivia Parker
Couple sharing a warm first date at a modern restaurant table

I met Daniel at a taco spot on Sixth Street at 7:15 on a Thursday. Forty minutes in, he said he could see himself marrying someone like me. My stomach flipped and I could not tell if that was excitement or a warning. Five years later, I finally know how to tell the two apart. … Read more

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What to Do When He Wants to Hang Out Instead of Date

October 9, 2026September 28, 2026 by Olivia Parker
Woman smiling while texting on her phone

Theo texted me “wanna hang out this weekend” nine days after we matched on an app. I stared at that word for way too long. Hang out could mean anything from a movie to a group bonfire with strangers. I did not know which one to expect that Friday. We were both twenty-four and neither … Read more

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What to Do When He Cancels Your Third Date in a Row

September 20, 2026 by Olivia Parker
Woman looking at her phone feeling let down after a canceled date

My friend Priya called me at 9:15 on a Sunday night, annoyed. Nolan had just canceled their third date in a row. She met him on a hiking app three weeks earlier in Portland. Every date felt promising until the cancel text arrived. This time his excuse was a sick roommate he had never mentioned. … Read more

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What to Do When He Looks Nothing Like His Dating App Photos

September 19, 2026 by Olivia Parker

My friend Renata texted me from a brunch spot bathroom at 11:20 on a Sunday. She had been sitting across from her match for six minutes. Her message that morning was only five words long. She typed it fast: I almost walked back out. Cole looked like a different person than his photos showed. Same … Read more

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What to Do When He Texts All Week but Never Asks You Out

September 28, 2026September 17, 2026 by Olivia Parker
Woman alone at a cafe window checking her phone while he texts all week but never asks her out

My friend Marisol met me for coffee at 7:15 on a Saturday morning. Her phone sat face up on the table the whole hour. She had been texting a guy named Trevor for five straight weeks. They had never once been in the same room. She showed me his last message and read it out … Read more

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Olivia Parker

Relationship writer sharing honest, lived-in stories about love and distance.

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