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Usually somewhere between a 20-30 lb loss is when I have had people comment. Very noticeable in your pics. In my experience it takes guys much longer to comment/notice, with guys being usually less observant/communicative to begin with.
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Buy him a video game 'stead of a tool. That's his love language...Shheeeesh.
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Also love German Chocolate! I've got to start bringing food in too. I go out way too much. Eating ok when I go out, but I'm eating the same stuff all the time (Dunkin donuts egg-white flatbread, slice of pizza, etc). Spending too much $$.