I’ve been trying to write this post for hours now. I have a block in my head. Harry is one of the closest friend of my sister’s husband. The crossroad of family (or close friends) and dating can get really messy really fast.

My sister’s husband had this idea of potentially setting us up for a while. When I stayed with them a few months ago, he “very innocently” invited Harry over for dinner. Unfortunately he didn’t tell me about his plans…without knowing it, I bailed on Harry, as I stayed out late with some of my friends and only came back long after he had left.

The second try went smoother. My sister, her husband, Valentina, Harry and I had dinner together a few weeks ago. It was a great evening and by the end of it Harry suggested that the two of us should have lunch at his favorite Italian place some time.

Setting up this “date” (?!?!) followed Germany efficiency. A few text messages and we were all set. It was another beautiful day in Berlin and we met on the terrace of a Thai restaurant. It could have been a bit awkward, neither of us knew what my sister and her husband had told the other. But it wasn’t. It was a great lunch. Harry did the lion share of talking (which most men do during the 1st date, I think). I didn’t mind however. I felt that he needed needed to get some thoughts regarding his career and the next step off his chest. Always happy to talk business. And it was an easy subject to ease us into our “date”.

After lunch we went to a café to get an espresso and ran into Valentina. She was on Tinder and helped us to finally open up a bit more and talk about dating. It was great to get to know the entertaining side of Harry.

By the end of the date, Harry invited us over to his family vacation home in Italy. We will pass by on our way to Siciliy anyways, where Valentina and I will spend August. I usually have a very good intuition of how men feel about me. Did he invite us because he wants to spend more time together? Or simply because he’s almost part of my extended family?

With Harry, I am absolutely clueless however. I can’t read him. Or maybe I don’t want to read him, because anything above and beyond being friends could lead to drama real quick. More to follow…it looks like we’ll visit him in Italy next week!