Dear Wendy: “I Got Hot And My Boyfriend Isn’t Happy About It”

My boyfriend and I have been together for a little under two years. About eight 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, which makes my boyfriend 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 breakup, 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 him how much I want to be with him, or is this a dealbreaker? — Hotter Now

I wouldn’t say it’s necessarily a dealbreaker without first talking to him about how much his attitude is bothering you and giving him a chance to get over it. You’re on the right track with reminding him how much you want to be with him, but more than that you need to make it clear that while you respect that he may need a little time to adjust to the new you, you absolutely will not tolerate him trying to control you. This business of him telling you what to wear has to stop; you’re not his child. Furthermore, you worked hard for your body and you deserve the reward of feeling good about yourself without someone making you feel guilty. After all, you got in shape for yourself. You didn’t do it for him and you certainly didn’t do it for random male admirers. You did it for you and if your partner can’t celebrate you reaching a personal goal, you need to talk to him about how much that bothers you.

I’d also advise you reiterate how attracted you still are to your boyfriend and how happy you are with your sex life, but let him know if he’s interested in joining you on some of your workouts, you’d be happy to have the company. It may be that he’s a little jealous of your weight loss and wishes he could do achieve the same success. Without making him feel bad about how he looks now, you could talk to him about how great it’s felt to take control of your body and get healthy. Perhaps a little motivation on your part would go a long way for him. But, if he declines your offer to help him get in shape and he continues his crappy, disrespectful behavior, you might want to kick him to the curb. Who needs to be weighed down like that?

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 can be quite friendly and outgoing, but when it comes to going up to a random stranger on my own, I absolutely freeze. This is even worse when it comes to guys I like. I can’t say a single word to them at all. I’m so afraid that they’ll think I’m flirting, and won’t want anything to do with me because they don’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

If you feel especially shy talking with guys you like, why don’t you practice with guys you aren’t interested in? Start making small talk with cashiers at the grocery store, your classmates, neighbors you run into by the mailboxes. You don’t have to have full-on, in-depth conversations here. We’re talking chit-chat about the weather, a big game everyone’s talking about, maybe an upcoming test you’ve been studying for. Getting over shyness takes practice and the more you shoot the crap with random people, the more natural it’s going to feel and the easier it’s going to be approaching someone you are interested in.

Getting over your low self-esteem is going to take a little more work. When I’ve felt self-conscious in the past, it’s helped me a great deal to get into a regular exercise routine. Not only so I start shedding pounds, which gives me a boost in confidence, the released endorphins increase my feel-good energy. Add a healthy diet to the program and I quickly notice clearer skin, shinier hair, and brighter eyes. And when I look good, I feel good. And when I feel good, I’m more social, and less likely to stay home or hiding in a corner feeling sorry for myself.

I’d also recommend signing up for online dating. Yes, it requires putting yourself out there, but the risk to your ego isn’t as great because there isn’t any face-to-face rejection. You post a great picture of yourself, write a few interesting things about who you are, and wait for anyone who might be interested to reach out to you. There are even dating sites specifically for people who are overweight, so you can rest assured that for anyone perusing those sites, your weight won’t be a detriment. In fact, it may actually be a turn-on. I spoke to a close friend of mine who happens to be overweight and felt similarly self-conscious when she was your age. She recommended a couple dating sites that got her positive attention and helped her feel more confident (even when she didn’t always find guys in her area she was interested in dating): and Another piece of advice she passed along is to try therapy. “Therapy helped me more than anything else to get over my self-esteem issues,” she said. Good luck!

Follow me on Twitter and get relationship tips and updates on new Dear Wendy columns!

*If you have a relationship/dating question I can help answer, send me your letters at {encode=”[email protected]” title=”[email protected]”}.