I know this is a tough ask of Reddit, but please try to be understanding and non-judgmental. Keep in mind that I am terrible at flirting and am a bit new to it.

So, yeah, basically what the title says. Sometimes when I wake up, I’ll send her a (SFW) selfie, and say, “good morning, cutie ☺️❤️”, and she sometimes compliments me back. Today I sent her one of me in jeans and an unbuttoned shirt, I’ll see what she says.

I think it would be really fun to flirt or sext. Hell, I even enjoy talking about sex with women in a non-flirty way, because it’s an interesting topic. But I feel like it’s hard to ask a woman about her sexual desires/life without coming across as either pervy or judgmental. For example, I feel as though an icebreaker such as “how much sex have you had?” is too forward and could come across as slut-shaming.

Any advice is welcome. Thank you! 🙂

1 comment
  1. Yeah, definitely don’t ask her how much sex she’s had. That’s not an icebreaker, it’s creepy.

    I’d suggest keeping it to light and friendly flirting until she’s expressed in person that she’s interested in more. If you start talking or hinting at sex and she’s not ready for that, it’s going to scare her off. It’s also a lot harder to read tone through text and something might come off as a lot creepier than you thought. Compliment her appearance (cute, pretty and beautiful are better than hot and sexy for now), let her know you’re enjoying spending time with her, etc. Next time you see her, try making light physical contact like putting a hand on her upper back while you hold a door for her, or touching your arms while you sit side by side. Make eye contact. Smile. Ask thoughtful questions about her interests (NOT sexual interests). If she reciprocates the physical contact, eye contact, smiles, compliments,etc. , you can progress from there.

    Sexting might seem exciting (and it definitely can be when it’s right), it’s not something that you want to rush. My opinion is that (with a few exceptions) it is better not to text about sexual acts until after you’ve done them in person.

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