Some years ago a younger girl I worked with was complaining to me that no one had asked her out for valentines day, i knew she was baiting me to ask her. She was pretty attractive but there was an age difference (at the time she was a junior in high school, I was 22) so I wasn't trying to get involved with her. As the day came and she was still baiting me and saying how she was going to spend valentine's day alone I eventually gave in and thought to myself "why not, an innocent dinner won't hurt anyone and it may give her the boost in self confidence she was needing". So I told her that I'll pick her up for dinner.
I was trying to keep everything at arms length, not wanting her to get too comfortable with me but at the same time giving her a good valentine's day experience. I bought her chocolate and some cheap flowers I picked up from a grocery store. I picked her up, she looked stunning and we went to lo sole mio as it was her mom's suggestion.
It was a last minute deal, they were crowded and many people must have made reservations well in advance. We showed up and asked for a table and they put us down on a list. We talked as we waited, I was still trying to keep it friendly but not romantic. We were finally seated at a table in the middle of the restaurant and I could tell that she was nervous, she was fidgeting with her napkin and plate, she barely ate any of the apetizer. The conversation had some awkward silences as I tried to lighten the mood and still keep it as friends. The dinner came, it was delicious!
After dinner I drove her home, in her mind it was probably a complete failure of a date and if I was aiming for it to be a date it would have been a failure with awkward pauses, nothing was planned, going straight home after dinner, and there wasn't much romantic talk. I got out of my car to walk her to the door and she gave me a hug, I hugged back. She then kissed me on the cheek and said thank you. I figured I was successful in keeping it as a dinner between two friends and helping her gain some confidence. I was wrong, we didnt stay friends much longer after. 7 years later to present day, we are now married and have a kid on the way.