A Memorable First Date with the College Freshman (Update)
Some of you asked for an update on this situation, so here it goes. (TL;DR: A college freshman approached me at a music event, we hit it off, exchanged numbers, and a few days later, she reached out to text.)
I’m thankful for all the feedback, especially from a user named u/autonomyfairy. The advice really helped me frame my mindset around dating someone like her, and I’ve taken that perspective to heart.
Our First Date
After a few text exchanges, she sent me a selfie of herself in a cute outfit. I was taken aback by how adorable she looked, and it felt like the perfect opportunity to step things up. I offered to buy her the outfit and take her out to dinner. She responded with excitement, and we made plans for the next night.
I met her at the store, and she was dressed casually but effortlessly stylish. Her hair was perfectly done, and she wore minimal makeup, which only enhanced her natural beauty. She greeted me with a big, genuine hug, and I couldn’t help but feel an instant connection. She tried on the outfit I’d offered to buy her—this black-and-white striped crop top with a tiny skirt that really highlighted her curves. She twirled around, asking for my opinion, and I told her it was made for her. She smiled, kissed me on the cheek, and I happily paid for the outfit, also picking up a pair of white heels to complete the look. She left the store wearing it all, looking absolutely stunning.
Dinner and the First Gesture
We headed to my favorite upscale Italian restaurant. We definitely caught some eyes from other diners, but that didn’t seem to faze her one bit. I’m used to the attention, but she handled it with effortless grace. We sat down and ordered drinks—both of us sticking with non-alcoholic options for the night.
The idea of sugar never really came up between us, and I didn’t want to assume anything. However, I did want to gift her something thoughtful, so I handed her an envelope with a generous amount of spending money. I told her it was for her to treat herself, and the look on her face was priceless. Her eyes widened as she peeked inside, and I could tell I’d made the right call.
Dinner was delightful. We chatted about school, her family, and what life was like for her as a freshman. She was definitely playing the flirt, leaning in close, brushing her hand against mine, making the whole dinner feel playful and intimate.
The Hotel and Beyond
Over dessert, she surprised me by asking if we could go somewhere “private.” I wasn’t fully expecting intimacy on our first date, but I had reserved a hotel room just in case. She seemed eager, hugging my arm as we left the restaurant. I could tell this was turning into something special.
I won’t go into explicit detail about the hotel, but I can say this: I made sure to treat her with care and attentiveness, prioritizing her comfort and pleasure above all. The experience was filled with sweetness and tenderness, and in between our time together, we continued to talk and connect on a deeper level. She mentioned that her past boyfriends, guys her age, hadn’t been able to offer her this kind of experience, and that only made the night feel even more rewarding.
We spent a good four hours together, just enjoying each other’s company in every way possible. By the time we parted ways, I felt like I had made a real connection with her.
Reflections and Looking Ahead
I’ve had a serious spring in my step ever since. Even my wife, who knows about my arrangements (we have a “don’t ask, don’t tell” policy), noticed how much happier I’ve been. It’s a strange feeling, but a good one.
I’m seeing her again tomorrow night, and I’m genuinely excited to spend more time with her. It’s refreshing to connect with someone so young, so vibrant, and so full of life. I’m looking forward to what the future holds for us.
This experience has reminded me of the importance of keeping things fresh, fun, and respectful. It’s about mutual enjoyment and understanding, and that’s exactly what I’ve found with her. I can’t wait to see what’s next.
