How do I subtly flirt/flatter with a shy female friend? I would like to complement her a little bit, after a month I'm going to ask her out?

[Anonymous]

Our small social group just broke up and were getting used to talking one on one. We would only really talk while in a group. I would like to subtly and lightly flirt with her for about a month while we get used to talking with each other. So that after a while I can ask her out. That way she will hopefully have gotten the hint by then that I like her and she won't be surprised when I ask her out

Updates

+1 y

Any suggestions on how I can start making physical contact with her more?

[DaniRockerlml]

For a shy girl, being nice is the smartest thing you can do. Make her feel calm and secure around you. Once that step is mastered, eye contact, smiles and subtle touch. Then, compliments. By then, she should have gotten the hint and if you see reprocification (a. k. a blushes, nervousness) totally ask her out!
Good luck! : )

[Asker]

Thanks for the great opinion DaniRocker. Currently I'm doing pretty good in making her feel calm and somewhat secure around me. I'm not really sure how to make her feel more secure around me though. We both make eye contact and smile while talking or playing games. However I have no idea on how to subtly touch her. Other than giving her a hug goodbye. Last time I texted her I'm not sure why but she got somewhat flustered and she is already usually nervous when we talk in person. Any more good suggestions?

[DaniRockerlml]

I can say from personal experience that when you're shy, hugs are the best thing in the world. So maybe hugging her a cupple times a day would be cool or gentle tickles when you're playing around.
As for the texting part, texting a lot might be overwhelming for her and what you could do for that matter is to always talk about something she knows and likes. It could be a tv show, a movie genre...
Because it is intimidating to run out of replies and having the conversation to become awkward.
Another strategy for this is to text her about something that just happened to you (it could be real or make it up). For example, your babysat your neighbor's kid and it got of of controlled or whatever really, as long as it's light. That away, replies never run out and she will not feel nervous.
Hope that helped again and if you have any more doubts feel free to ask : D

[Asker]

Yeah that did help. especially with the conversation getting intimidating part because that is kind of our current problem. It is also why we mostly likely just talked in groups before. If we ran out of things to talk about we just let the others take up the conversation. I'm still not sure how to initiate tickling her. Mostly because were never really joking in that kind of way but also because I'm not ticklish. I just pretend to be so my mother will stop tickling me when she starts. It is kind of fun but it is definitely over quicker when I fake it than it is for her to try and find my tickle spot only to give up.

[DaniRockerlml]

Lol. Then definetely start joking around, because otherwise it should be hard to set the flirty atmosphere between you two.

[Asker]

Yeah it will be thanks for the help.

[Asker]

O how do I tell her I like you shyness/nervousness from her normal nervousness?

[Sexymofo12]

tell her you like something about her (like her eyes, hair, shoes)

[Asker]

Thanks I do try and complement her when I see that she has changed something. Sadly she usually wears the same thing like I do. So unless she gets a new haircut or paints her nails there is not really anything to complement.

[Asker]

Any other suggestion?