I Thought Something Was Amish

Here's the origin.

DEAR JERKASS: I met a guy four months ago. Our relationship is new and pretty casual for the most part. We like each other's company and spend nights together, but when we're intimate, he keeps his clothes on -- boxers and all. He is only 26, but he has told me about past relationships, so I know he has had experience.

Over the past two years he has lost almost 100 pounds. He looks great now -- healthy and toned. I have seen him get in and out of the shower. (I noticed a little excess skin on his stomach, but not much.) It's really weird. I don't feel comfortable taking my own clothes off when he doesn't.

This isn't exactly a deal breaker for me, as I obviously am attracted to him. I just would like him to be comfortable with me. Should I address this with him, and if so, how? Or should I just leave it be for now? -- AWKWARD SITUATION IN GEORGIA

DEAR AMISH,
It's not a deal breaker and you are attracted to him....seems like you have your answer.
If you want to be pedantic about it, you could either walk around naked until he does, or wear his boxers on sex nights.
OR like any relationship that is successful, you can take your own advice and talk to him about it, as well as offering compliments every time he shows a bit of extra skin.
But if you keep bringing it up and it pisses him off, back off and just let him be comfortable.  The relationship will definitely take a down turn if you keep picking at him.