Woman Goes on Date with Man, When She Rejects His Advances, He Asks Her to Pay Him Back

A woman recently sought advice from the Reddit community after a man she had gone on a date with sent her a surprising request — he wanted her to pay him back for part of their weekend together.

In her post, she explained that the pair spent three days together after he invited her out on a Friday, Saturday, and Sunday. Everything seemed fine until, some time later, she woke up to a text from him that left her stunned.

“Good morning. I hope you had a fun weekend. The total from the other weekend was $212, your half comes to $106, minus whatever you covered at Bitter & Twisted. Go ahead and send it over on Apple Pay or if there’s a different platform you use let me know,” she recalled him writing.

According to her, the man covered most of the weekend’s costs, but she had already paid $70 at a bar and $40 for downtown parking. “He kept insisting on going to the next place each time we finished the place we were at,” she wrote, emphasizing that they had never agreed to split expenses.

She added that on Sunday night, he invited her over to watch a movie, though “nothing happened.” Later that week, he asked her to come by again and suggested she spend the night. She declined the overnight invitation but agreed to another movie.

“As we watched the movie he kissed me, I felt uncomfortable since it seemed like he wanted to do a little extra, and left,” she shared. “Granted it was 3 a.m.”

The next day, he didn’t reach out — and nearly five days later, she received the text asking for his share of the weekend costs.

“Never did we agree we were splitting the bill,” she wrote, suggesting that the timing made it seem like he was upset she had rejected him. “It seemed like the rejection had him feeling salty about spending money on a weekend on me.”

She also noted that her own contributions already came close to the amount he was demanding. “I didn’t plan on asking to split that amount because it’s tacky,” she said, before asking readers, “but am I wrong for sending ‘my half’?”

One male commenter said he couldn’t “imagine acting like this” toward a woman. He added that if money was a concern, “he should just explain as much and ask if you mind covering the upcoming date, or suggest a more low key/cheaper date.”

Another reader agreed that the man’s actions were a red flag. “Honestly, if you never agreed beforehand to split costs, it’s kind of rude for him to spring that on you after the fact,” they wrote. “Especially waiting days just to drop that in your lap.”

The woman later responded to clarify her stance. “Before I went over, I told him, ‘nothing is going to happen, you asking me to sleep over seems like you want something that I don’t want rn.’”

Despite setting that boundary, she said she still felt pressured. “I don’t know if he just disregarded it and still felt entitled to try or what, but definitely crossed my boundaries knowing that, that’s not what I wanted to do,” she concluded.