Hello! I (38f) mustered up some courage today and asked a man out who I see fairly often in my life. I asked “Would you like to go to dinner with me sometime?” I wonder if maybe I caught him off guard in doing this, but he’s been flirty with me in the past so I decided to take a chance.

Admittedly he was doing something when I asked and looked a little surprised, and his response was “possibly” so I handed him a card with my number on it and asked him to maybe text me and let me know.

I am leaning towards taking this as a no from him, which is perfectly fine, and I am not anticipating a text from him. I would like some input on this though. I am admittedly very embarrassed at this moment and wonder if I read his flirtiness wrong.

Edited for grammar.

Edit: I want to thank everyone who commented for their kind words and encouragement. I am tired of OLD, I don’t even have any dating apps, and I wanted to pursue someone I felt comfortable with in person instead. I’ve been considering approaching him for a few weeks now. If it doesn’t pan out, that’s ok, he’s still a genuinely nice man and I don’t take it personally or regret asking.

Here are what netizens think:

I ask women out all the time and often times that results in them feeling uncomfortable and not giving me a clear no. It stinks getting the weird answer, but I’m glad I asked because the answer could’ve been a “yes”.

There’s nothing different with me asking a woman out and a woman asking a man out. Both of us have the chance of getting rejected and us asking didn’t change their interest. If they were interested, they would’ve said yes. So just like I won’t get discouraged asking women out, you shouldn’t get discouraged. You’re looking for someone who’s excited at the idea of meeting the real you, so don’t shy away from asking them out and showing them the real you.

Let me just say that with age usually comes courage – when I was 32, I was pretty shy about approaching guys and really had to fake the confidence. I always felt nerdy and awkward and like I’d come across as desperate. But now? Totally different. Now at 38, I just shot my shot 2x in the same week with 2 different guys, yolo!