Dear wendy 7/23

My boyfriend and I have been together for a little under two years. About 8 months ago, I’d gained some weight, so I decided to get off my butt and start getting back into shape. Before, my boyfriend and I were both cute but decidedly chubby. Since then, I’ve lost about 30 lbs, my awkward hair grew out, and my skin has cleared up. I’ve always been very busty and didn’t lose any of it, and through sheer luck, I ended up with a “Joan Holloway” type figure. For the first time in my life, I feel really confident and love my body, and it’s the first time I fit what’s considered attractive by society. My boyfriend, though, has become very insecure. He’s just as sexy and wonderful as the day I met him, but he seems to be obsessed with the thought of me leaving him for someone “hotter”. He constantly worries that people wonder why I’m with him. On top of that, I’ve started getting a lot of unsolicited male attention–not just the typical cat callers, but being checked out, smiled/waved at, etc. I don’t like it, but my boyfriend has become obsessed with it. If we go out and he sees men looking at me, he gets sad and mopey. He worries about how visible my cleavage is, and discouraged me from buying a bikini, even though it was a modest vintage style one. Normally, this kind of behavior would earn him a break up, but he’s never shown any questionable behavior in the past, and our sex life is as awesome as ever. Should I chalk it up to insecurity and give him a chance to get over it, while encouraging him and reminding me how much I want to be with him, or is this a dealbreaker? I am 20 years old, and am about to begin my junior year in college. I am noticeably overweight (but not obese), and therefore have very low self-esteem. Because of this, I am extremely shy. When I’m with a group of people, I’m usually able to function socially, and I’m told I can be quite friendly and outgoing. But when it involves me going up, on my own, to a random stranger, I absolutely freeze. This is even worse when it comes to guys I like. I cannot talk to them. And I don’t mean I can’t talk to them without being awkward. I can’t say a single word to them at all. I’m so afraid that he will think I’m flirting with him, then not want anything to do with me because he doesn’t like me in that way. (this has happened to me several times throughout high school and the last two years, and it’s always devastating). My best friend has assured me I’m over-analyzing things, but I still can’t bring myself to start a conversation. I’ve been told to ‘just suck it up and do it’, but is there any way I can ease into things gradually? -wallflower

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