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I was SO excited. I got super dressed-up and went to the campus bar to meet him. I guess I drunkenly gave my number to a random guy at a party who happened to have the same name as this cute guy in my architecture class. It was super embarrassing but I made myself stick it out with a smile until the date ended. I meant the one in my apartment.

Hilarious and Bad First Date Stories | StyleCaster

He never even offered to buy me a drink! I was already into this guy—his pictures were cute and the texting was good. He was the quiet, brooding, artistic type back then, and I was hoping he still was. When we first met up, everything seemed fine—he was outfitted as a hipster and even had a good job. We spent the first hour date catching up, and then all of a sudden he got really serious and started taking me through his murky family health history: He spent all night chain-smoking, getting me very drunk, and then lunged in for a kiss before hopping on a bus home. He texted right away to make plans for a second date.


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She ended one relationship, and the other two men disappeared shortly after sex. How did this happen?

The Perks—and Challenges—of Dating a Much Older Man

Courtney wanted things to happen organically. Ian was great fun to be around. He focused on Courtney and gave her a lot of attention.

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Courtney liked David best of all. At 30, he was serious about his career and openly stated he was dating to meet his future wife.

The Perks—and Challenges—of Dating a Much Older Man

He said from the beginning that he wanted to move things forward but at a very gradual pace. He did not pressure Courtney for sex at all. He understood that was not fair since he was being careful about emotional intimacy. After 16 very fun dates he told Courtney he was ready to become more serious.

Courtney had met David on Tinder, and they had a mutual Facebook friend. When Courtney asked her friend what she knew about David, she learned that he had been heartbroken when his ex cheated on him last year. Courtney is not promiscuous by any means, and has never had casual sex in the strict sense of the word. She felt comfortable and assured that she was building something real with each of these men.

13 Funny First Date Stories That’ll Make You Crack Up

And yet, she was mistaken. Now she feels emotionally exhausted and discouraged. Dating is shopping for your life partner. You will most likely date several people before you meet the person you choose to marry. But when each of those relationships destroys a piece of your soul, it takes a toll on your outlook and your emotional well-being.

You will attract men who are drawn to that. Courtney failed to fully evaluate and understand her own feelings before sex, as well as those of her partner.


  1. Dating Older Men: The Perks and the Challenges | StyleCaster.
  2. 13 Funny First Date Stories That’ll Make You Crack Up;
  3. 32 People On Their Worst Online Dating Experience.

She failed to notice that he saw her as an attractive woman on his arm rather than someone he might become intimately connected to. David made it clear he was auditioning Courtney for the role of wife, and he indicated she was passing all his tests with flying colors. She may have been acing his tests, but they would continue forever. What would have lessened or even eliminated the disappointment and rejection Courtney eventually felt?