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Will it get awkward if she doesn’t feel the same? Or is it a relatively safe way to play it?
Depends on the person. If you’re unsure do it in a cute playful way.
How do I make it cute and playful?
Something like “Merry Christmas (name)! I miss you x”
It’s in the way you do it rather than what you say really, which is hard to convey over text unless you know each other well like that. Just go with what feels right for you.
Well I kind of want to be a bit flirty but don’t want to make her too uncomfortable. It’s a hard balance.
It’s not really, just do what you’d like to do and gage her reaction. If you’re right for each other it’ll flowZ if you’re not it won’t no matter what you do.
I’m always worried about making her feel uncomfortable. I told a friend that and he said she wouldn’t spend so much time with me if that was the case.
Life is all about being bold, taking chances and having no regrets. You live and learn through experience, if you’re too afraid of making mistakes you’ll never know and will have regrets instead. It’s your call.
That’s very true. But it’s just that she’s such a great girl and I hope I can at least be friends with her. She’s not the type of girl I normally find physically attractive.
If she really is such a great girl you won’t be able to go far wrong.