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I was on a day date today and she asked me this twice during the three hours we spent together. The date was going well and I was genuinely enjoying myself, we were having a great day so I wasn't giving out an unsure vibe.
The first time I answered simply "I am, it's easy to have a good time with great weather and great company". In response she smiled and put her hand on my chest.
I wasn't sure how to deal with the question a second time, her asking again caught me off guard. I gently teased her about asking for a second time (I was gentle because I figured she might have felt insecure and didn't want to collapse her ego with anything too heavy handed). This lead into more playful banter so it went ok.
I've never come across a girl who has asked this before during the actual date, has anyone else experienced the same thing?
It is possibly over-analysis to look into it further because it is most likely a throw away comment and small talk she was making and nothing more but the forum's opinion on matters are always enlightening.
She's a bit insecure which in this case is a good thing. A simple good answer that iv used in the past is "I always have a good time" and smile or even a cheeky wink with it... lol