Dating Diaries: Meeting at the hotel was a turning point

Lindsay is a 32 year old teacher who lives in the West End. She says, “My style is eclectic and feminine. I like to pair sneakers with a feminine dress or skirt, or wear jeans with a silk tunic that looks like a flowing bathrobe. My look is down-to-earth but playful. Lindsay says her friends and family would describe her as “funny, outgoing, loving and lovable, scatterbrained, a bit of a bookworm, with an adventurous spirit.” She enjoys “long winding walks, reading, writing in my diary, watching high-profile TV shows, and rewatching movies from the 90s and 2000s.” Before dating Aaron, Lindsay had been single for “almost three years, my longest time ever.” She says she’s looking for someone who is “genuine, kind, smart, and interested in the world.”

Aaron and I had known each other since college, where we became close friends. I never imagined anything serious happening with him because he had a girlfriend all the time.

When they broke up, Aaron had another serious relationship. After that, we started chatting more. I thought he was looking for support as he recovered from his last relationship, but we grew closer and closer and I started to think maybe we had something real. He told me that he had always found me intriguing and that he remembered things I had said or done years before. I was blown away by that.

It was very natural when our friendship turned into a long-distance relationship. We started seeing each other every few weeks. I was living with my parents at the time and had more flexibility to drive to see it. He had moved to a small town for a work assignment at that time. During my visit, we watched movies, cooked, had sex and laughed a lot.

Once things were sort of settled, I started hoping that Aaron would become my “last stop” in terms of dating. Our relationship was already filled with fun, laughter and sweetness, but I was ready to take things in a more serious direction.

I suggested that Aaron come visit me, that we check into a hotel room in town, and have a suitable date. I told him I would organize everything and he was definitely up for it. I found a deal on a cool hotel room package and told him where to go and when.

I was definitely more nervous than usual. The date felt like a turning point. I packed a big suitcase with all my beauty stuff and felt like I was going to the Oscars. I had carefully chosen my clothes at home. I had invested a lot in this date.

When Aaron arrived, the energy between us was incredible. The first thing we did was open the champagne I had packed. I had cooled it at home and continued to cool it at the hotel. It was a bit difficult to open it because neither of us drinks that much champagne, but even that was fun for us.

From there, I finished getting ready and we went out to dinner. I had made a reservation in a nearby neighborhood so we had the opportunity to walk together, get rid of some nerves and enjoy the sights and sounds. I felt good. It was special to be with Aaron; he’s just one of those people. He held and caressed my hands, and thanked me profusely for organizing the evening.

Aaron suggested having a drink at the hotel bar. They had some interesting cocktails and we had a great time talking to the bartender. I was having so much fun.

Eventually we made our way to the bedroom, where we made out and then got to work. As I fell asleep next to him, I felt like a real adult, which doesn’t happen too often!

In the morning we had breakfast in the hotel restaurant. The food was amazing and Aaron gave me props to set it up. He seemed genuinely impressed with everything and was even more affectionate than usual that morning. Usually the next morning is when the guys are “cooling off” from what I can tell. We kissed goodbye and I went home feeling amazing. I had no idea what the future held for us, but it felt like our relationship had changed overnight.

Lindsay rates her date (out of 10): 8

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