Pursuing a romantic interest in a friend’s parent introduces a level of complexity that can permanently damage the trust and comfort of the existing dynamic. If you asked your friend’s parent out on a date but they rejected you, what would you do?
This man is in his early 20s, and he has a friend with a single mom in her mid-40s who hasn’t dated a guy in several years. He’s not going to lie, he’s always had the hots for his friend’s mom, but didn’t do anything about it.
“She carries herself with confidence and has a pretty wicked sense of humor. For most people who do not know her, she can seem pretty cold, detached, and aloof, but once you get to know her, she is one of the nicest and most caring [people] out there,” he explained.
“I have been strongly infatuated with her for the last 2 years. Recently, I ran into her in a shopping mall, and we had a great conversation.”
“She got both of us coffee, and we had a good time yapping away at the cafe. Ever since, she has appeared in my dream twice. I have never felt like this towards any other woman before, not in the last 22 years of my life.”
So, yesterday, he boldly decided to let his friend’s mom know that he’s interested in her by sliding into her DMs. He mentioned that an outfit of hers looked incredible on her.
Next, he invited her out to dinner, and she got back to him saying that sounded great and she would bring his friend (her son) with her.
He was confused and not quite sure how to respond. He was trying to tell her this was a date and meant exclusively for the two of them. He took a couple of hours to think it over.
“Then, I got a bottle of red wine and chugged 2 glasses down to calm my nerves and boost my confidence. Then, I texted her, telling her I would love to go on a date with her,” he continued.
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“Right after I sent that, it was radio silence from her [until] 1 hour ago. She dropped me a text gently declining my offer and telling me I am a great kid, and all the best with girls my age.”
“I am absolutely crushed. I don’t know how my friend will see me from now [on]. I have no idea if she told my friend.”
Well, rejection is a part of life, and it’s a good lesson for him to learn while he’s still young. I’m sure his friend’s mom doesn’t want to do anything to gross her son out, so of course, she’s smart to turn him down.
Her inviting her son along for dinner was a subtle way of helping him get the hint; he just didn’t, and that’s ok. I doubt she will say anything to her son, which would only make it even more awkward than it already is.
At the end of the day, I don’t see anything wrong with him wanting to date older women, but he has to steer clear of his friends’ moms. That’s not a good pond to go fishing in.
What advice do you have for him?
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By Bre Avery Zacharski
Hi, I'm Bre, Chip Chick's CEO! I have a degree in Textile/Surface Design from The Fashion Institute of Technology, and... More about Bre Avery Zacharski
