TL:DR: I encouraged my office mate to let the guy she was dating finish on her face … then I did it too.
Tara and I were in grad school together and shared an office — basically they’d put 4 PhD students in what was one professor-sized office. She and I often found ourselves there alone together and became very close friends over a few years. We were both in our early-30s and I’d been married for a few years with a very happy marriage.
The story really starts when she and her long-time boyfriend broke up. They’d been dating nearly 10 years, and I think it basically ran its course, but it’s still traumatic when such a long relationship ends.
So as part of our friendship, I was consoling her and helping her through the end of her breakup. Just the usual telling her how great she was and letting her know it’ll all be okay. Then as she started dating again, I was kinda giving her the “guy’s” perspective on dating since she hadn’t really dated in 10 years … which led to giving her the guy’s perspective on sex. Tara was definitely not inexperienced, sexually, prior to her long-time BF, but things are different at 30 than in your late-teens/early 20s.