Should I Ask Her Out Again?

Kara Pound

Written by: Kara Pound

Kara Pound

Kara Pound is an award-winning journalist based in St. Augustine, Florida. She holds a bachelor's degree in journalism from Flagler College. Her work has been published in INKED, Natural Awakenings, Design Aglow, Memphis Flyer, Jacksonville Magazine, E/Environmental Magazine, and dozens more. Check out some of Kara's work at

Edited by: Lillian Castro

Lillian Castro

Lillian Guevara-Castro brings more than 30 years of journalism experience to ensure DatingAdvice articles have been edited for overall clarity, accuracy, and reader engagement. She has worked at The Atlanta Journal and Constitution, The Gwinnett Daily News, and The Gainesville Sun covering lifestyle topics.

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Reader Question:

OK, so around two years ago I was living in Canada and I met a girl for only one night. She was a friend of another girl who I will call Girl B.

I spent a lot of time getting drunk with Girl B. So when Girl A came to visit, we all went out for drinks. At the time, nothing was said or happened with Girl A, as she had a boyfriend and I was too busy having fun.

Roll on two years and I am now living in Sydney where both of the girls are from. Girl B, who I am closer to, invited me to a bar for drinks. She also invited Girl A. We had fun and messed around – flirting and stuff. At the end of the day, she and Girl B invited me and a friend to the beach the next day. More flirting at the beach, etc. At this point, I figured why not ask her out, so we had a talk via Facebook, as it was my only contact to her at the time.

After this, we arranged to meet in her part of town. We went out and fun was had I think by both of us. While we were waiting for my train, I kept her warm by hugging her, etc. But I did not make a move. That was my bad and all.

After this, we settled into a pattern of flirting as friends I guess. I saw her five more times and we always had fun, including play fighting, but still nothing. Then I moved away for work for a few months and tried to keep in touch via text. Sometimes she would get back to me that day or the next day, but then she just stopped. Since I have been back, I have seen her once. So I figured I would give it another go but to try and keep it relaxed. I used Facebook again.

Since then, I have not gotten anything back. I was thinking of asking her out again. Should I? And if I do, should I use Facebook or try to get her to meet me face to face and then do it?

Help a very confused man 🙂

-Greg W. (California)

Expert’s Answer:

Hey Greg,

Wow! You and Girl A have some history. That and I’m super jealous of all of your world traveling. It sounds like the two of you definitely gel when you’re together, so why not continue the effort and see where the relationship takes you? It also sounds like Girl A is a busy bee by not responding to texts and Facebook messages right away, so be patient with her and realize that she isn’t going to make you a priority until you ask to be. Act more like a potential boyfriend than just her crazy friend who play fights and likes to hit the bars.

You two have known each other for a while, but you need her to see you in a different light. You need her to say, “How has this amazing guy been right in front of my face the whole time and I didn’t realize that we’re meant for each other?”

Good luck and definitely let me know how it goes.

Thanks for reaching out!


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