My Friend Used To Be So Fat

Hmm, in this case, I don't think that's it.  I'm not saying he's a bad guy (he has my back on many such things),  but I think he just thinks it's an attention-getting story to fill five minutes of conversation.  In any event, while the positive implications you offer are one possibility, the total picture is much more ambiguous.  Many girls are instead going to think it means I was lazy and lacked self-control in the first place.  They might also (correctly) be suspicious about what I look like under the clothes, though my experience is that many girls haven't cared too much about how fat I was, so they probably don't care much about that either. Now, as someone else noted, at some relatively-early point, a girl is probably going to have to know about these things.  But not every person I meet at a party is going to reach that point, and I'd also prefer to raise the topic on my terms.