New Here? Welcome! Dear Wendy is a relationship advice blog. You can read about me here, peruse the archives here and read popular posts here. You can also follow along on Facebook and Instagram. If you have a relationship/dating question I can help answer, you can send me your letters at firstname.lastname@example.org (be sure to read these guidelines first). Thanks for visiting!
In a feature I call “Your Turn,” in which you, the readers, get to answer the question, I’m presenting the following letter without commentary from me:
I’m 28-years-old and six months ago I started dating a wonderful man. He’s 27, and treats me with more respect and kindness than all of my other exes combined. I am incredibly happy. I knew him socially before we began dating, so I was aware of his painful shyness. It took him several months to muster up the courage to ask me out, and I happily accepted. We had been dating for nearly a month, and in that time he had yet to try to kiss me, so one evening I suggested we get this over with and I planted one on him. He confessed a few days later that I was the first girl he’s ever asked on a second date. I may or may not have been his first kiss. I’m totally OK with being his first of many things, as he and I are in love and very happy together.
Here’s my predicament: we’re now six months into our relationship and we haven’t had any sexual contact beyond kissing. I would really like to move in the direction of sex, but I’m not sure how to proceed. I’m not lacking in sexual experience, but I’ve never had to make the first move. I’m 99.9% sure that he’s a virgin, and I don’t want to freak him out, but at the same time, we’re adults in a loving relationship and sex shouldn’t be a difficult topic of discussion. He’s shy and awkward, but I love him dearly, and I want to handle this in the best way possible because I hope to be with him for a very long time. — Ready for More