Personal Health

The Top 50 Flirty Questions To Ask A Girl You’re Interested In

One of life’s greatest pleasures is finding someone to crush on (especially a person who’s worth your attention in this *climate*). And when you catch a vibe? Oh those butterflies are fluttering. Now, it’s time to turn up the heat.

Whether you’re getting to know another person on an app or are already a couple dates in, asking flirty questions can help deepen your connection. “Breaking past small talk helps you understand a person as an individual, and what makes them feel safe and comfortable,” says polyamorous educator and sex activist Tiana Peters. It’s not only a chance to learn about their desires, but gives space to yours, too.

Before you go there with a woman, Peters recommends considering the mood and setting of the convo, and adjusting accordingly. Are you in line at Shake Shack? On a walk in a quiet park? Did she just go through a breakup?

Asking flirty questions is magical, but the last thing you want to do is make the other person feel uncomfortable. Keep an eye on body language and nonverbal cues like eye contact, or if they’re leaning in or away. Another suggestion? Getting flirtatious over a fun date night activity like cooking or sharing a meal together gives both of you time and space to consider these questions carefully, Peters says.

Even when the chemistry is on another level, verbal consent is a must if you’re introducing more erotic questions. Ask, “Would you be open to me asking you an intimate question?” to open up the space to shift the conversation, Peters says. “You don’t know what people’s past traumas are, and it’s great to be aware and respectful of that.”

So, where should you begin with the questions for another woman? Simple q’s that provoke thought or introspection, says relationship expert Amber Kelleher-Andrews. Think desires (fantasies! kinks! orgasms!) or prompts about dreams, life perspectives, or relationship qualities. If you’re texting, try setting the scene with a visual (“It’s been a long day and I’m running a bath. Can I call you later?”) and save the in-depth curiosities for when you’re together.

Remember that good communication is a two-way street, too. “When I go to ask someone something more personal, I like to share something about myself to open up that vulnerability for that level of verbal intimacy,” Peters says.

Here are 50 flirty questions (we went for a mix of romantic, personal, and sexual) to ask a woman in order to build intimacy, learn about your partner, and have a little playful banter. And now, it’s sexy Q&A time!

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