Expert Dating Advice Needed

[EthanW.]

Hey, all. I've been out of the dating arena for a long while, and I thought I might try it out now that I'm more grounded in who I am and what I want.

So, I need to know some high level, professional dating advice....

When do I deploy the winky face to a girl?

Disclaimer: We've been on two outings already, and I'm definitely not looking for sex here. I just want a wholesome, get-to-know-you relationship.

 

[primaljade]

I've been around the block, and use the winky face regularly for these types of texts:

1.) If you don't know her well and you tell her a joke, and want to ensure she takes it as a joke.
2.) If you text a subtle double-entente that's dirty, not raunchy.
3.) If she texts you something cheeky, you can respond with ONLY the wink as a way to show you liked her response with minimal "energy".
4.) If you tease her in a fun way, and want to ensure she doesn't take it offensively/seriously.

Examples:
"Well, you got me, I'm a virgin "
"You should try being modest next time "
"I'm sure we can find something that fits "

Her: "You're such an asshole!"
Me:

 

[EthanW.]

@primaljade Ah, thank you, my dude.

I was going to use the wink with a positive comment toward her, because it was a little playful plus being sentimental. I wasn't sure, it seems to be a very powerful emotional report.

I'll be more selective with it.