Man wants to ask out woman that he previously rejected: ‘This caught me off guard’

A man wants to ask out a woman he previously rejected but is worried he missed his chance.

The man asked Reddit’s “Relationship Advice” forum whether he should go ahead and ask out his crush, or whether it’s too late for any possible romance between them.

Man and woman at a cafe.
Credit: Getty Images/Ezra Bailey

“I met this girl in [college],” the now-25-year-old writes. “My first impression of her was that she was quiet and awkward but extremely smart.” The man explains that he was in many of the same classes as the woman, and the two would often study together.

One day, while they were still attending college, the woman asked the man on a date. At the time, the man wasn’t romantically interested in the woman and rejected her.

“This caught me off guard and I just wasn’t into her so I turned her down and asked if we could remain as friends,” the man recalls.

Over the course of the next several years, the man and woman became increasingly close friends.

“We are better friends than before,” he explains. “She has become more comfortable with me and I can see more of who she really is.”

Now that the man has gotten to know the woman better, he has developed romantic feelings for her and wants to ask her on a date. However, he is worried that his previous rejection of her has made anything romantic between them impossible.

“I’m realizing that I have [messed] up,” he writes. “I want to ask her out but I’m afraid that I missed that chance. What should I do?”

“Be prepared for rejection.”

Many readers encouraged the man to ask the woman out but warned him that he might be rejected.

“Be prepared for rejection. It’s likely that once you rejected her, she worked to get over you and has done so successfully. Good luck,” one reader commented.

“You can try asking her out but also be prepared for a rejection,” another Redditor agreed.

“Go for it. But when you explain it, I wouldn’t go into anything about how you see her differently now. That can backfire,” another Redditor suggested.

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