I swore off online dating but, after 8 months without meeting anyone, I decided to give it another shot. Same story: few matches, most don’t reply, and those who do often fizzle out quickly.

However, I connected with a woman slightly older than me. She’s not my usual type (though I don’t really have one), but she’s natural, wholesome, and has been putting in real effort to communicate. She lives 45 minutes away, and we met in the city center. We hit it off, visited a few bars, and had a great time. She opened up, we had a quick hug and cheek kiss at the end (she almost missed her ride!), and she texted me afterward saying she had an amazing evening.

We’re meeting again tomorrow, this time in my neighborhood, which has great bars and my place isn’t far away (ahem). With this being only our second date, I want to escalate things and ideally have her stay over or at least stay late.

We’ve got good rapport, but I need to amp up the sexual tension while keeping her comfortable. I noticed her friends and sister were texting her during our last date, and she seemed even more excited after that, so I want to make sure things move forward without making her feel judged.

Any tips for escalating things naturally and ensuring the night ends on a high note for both of us? Preferably with her shooting various religious phrases at the top of her voice lol and maybe in time for her to catch her ride home if she can’t stay over