How would you feel if someone who had a crush on you decided to warn you about one of their physical features, just to test the waters and see if you would consider it a dealbreaker?
This 27-year-old woman has spent the last two years working with a 34-year-old man who is incredibly handsome. He’s also tall, looks nearly a decade younger than he is, has great hair, and a nice smile.
As for her, she’s not even close to being in this guy’s league. She says they’re polar opposites, since she’s not remotely in the realm of conventionally attractive. She’s just calling it like she sees it, but that doesn’t mean she has bad self-esteem.
She and her coworker have always been friendly with one another, and throughout the last month, he’s offered to drive her home after work is over.
“It started as a nice gesture, but last week he asked me out to get dinner, and we did. It was nice, but he didn’t call it a date or anything,” she explained.
“Tonight, when he pulled up to my place, he got noticeably uncomfortable and really serious. He said something like, ‘Hey. I need to tell you something and don’t want to waste you’re time if it’s a dealbreaker. I’m small. Like, really bad small. Take some time to think on it.. I won’t be upset either way, no pressure.'”
She felt shocked to hear him warn her about his size!
A couple of months ago, one of their other coworkers mentioned to her that her male coworker worried about his size confessed to never having slept with a woman before.
She thinks that tracks, as she has never seen her coworker with a woman or heard him talk about one in a romantic sense, which she suspects has to come down to his size.

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“Here’s the thing that’s really eating at me. He’s very kind and he remembers tiny things I told him almost a year ago, like about my brother’s job interview in Seattle, or that I don’t like pumpkin spice,” she added.
“I’ve also always felt I would catch him looking at me from time to time, but wrote it off as weird because he’s somewhat known as the weird, awkward guy around here.”
“I think I like him. But my biggest fear is that his honesty is directed at me because he’s looked at the situation and thought that I’m the safe option.”
She’s afraid that her coworker thinks that, since she’s not exactly pretty, she won’t leave him or be judgmental. She is also concerned that he wants to use her as some kind of practice run.
She has virtually no dating experience, and she only dated a guy seriously for around a year back when she was 24. Since then, she’s been painfully single, even though she’s come to accept being alone.
She’s left wondering how she can tell if her coworker truly likes her or is betting on her being some kind of safe choice in the love department.
“How do I figure out if his interest is genuine, or if it’s just born from years of insecurity and seeing me as the path of least resistance? Also… I don’t even know if I care about size,” she concluded.
I think he’s brave to give her the choice about such a touchy topic. It shows his vulnerability, and a lot of men feel ashamed about their size. He seems genuine to me, and I think she should give him a chance and see where it goes.
What advice do you have for her?
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