Hmm. I don't think losing weight to impress anyone other than yourself is a good idea. Say you lost the weight, and it didn't work out? You might start associating losing weight with trying to please other people, and failing. What if you lost the weight, got together with him, but always had in the back of your mind *well all well and good, but if I HADN'T lost the weight, how do I know he would still have wanted me?*
So I'd say totally dissociate your weight from attempt to rekindle romance. It can't be healthy to intermingle the two at all.
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