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How Can I Get My Serious Friend to Cut Loose?

Dear Sugar,

I have a friend who studies way too much and is so serious with his school work, but has the tendency to let loose every once in a while, although it has been quite some time since I have seen that side of him. He is coming to visit me for President's Day weekend and I want to drop some kind of "fun bomb" on him to make him less serious and more joyful.

Since I live in a warm climate, I was planning a weekend of water activities and outdoor sports, but wanted to ask if you had any ideas to help him connect with his fun side. He is really careful about how much he drinks and I don't want to compromise that, but any suggestions would be appreciated. Uptight Timmy

To see DEARSUGAR's answer

Dear Uptight Timmy,

How nice of you to plan such a fun filled weekend for your buddy, it sounds like he really needs to relax. Once he arrives, feel out what activities he is interested in and just play the weekend by ear. Being outside is bound to make him unwind a bit, so by all means explore those possibilities. Does he have any hobbies you could participate in together? Did he give you any ideas of how he wanted to spend his weekend?

Even though he isn't a big drinker, it sound like that doesn't deter him from the occasional wild streak, so make sure he feels comfortable and hopefully you can both let loose and have fun. A little R&R can go a long way so hopefully the sunshine will brighten up his mood and you can enjoy the fun weekend it sounds like he desperately needs.

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