Dear Wendy: “How Do I Tell Him He’s Too Fat To Date?”

This weekend is an all “Shortcuts” weekend for Dear Wendy. For every question, I’ll give my advice in two sentences or less, because sometimes the answer to a person’s question is so obvious and the need to hear it so great, being as clear and frank as possible is simply the best way to go. Today we discuss dating a fat guy, balancing friends, work and relationships, meeting the family, and dealing with a boyfriend who constantly brags about being hit on.

The guy I’m “sorta” dating is wonderful in almost every aspect. He’s incredibly sweet, considerate, a great listener and a lot of fun. There is one BIG problem though. He’s full-on overweight. It seems to not bother him at all: he’s super confident and sees no problem with the way he is. So am I just a big superficial bitch because I won’t date the fat guy? My friends all love him but always add that they think I’m “dating down” due to the disparity between our attractiveness. He’d be so cute if he’d just lose 30 lbs. How do I tell him, “You’re great, but I won’t date you because I’m not sexually attracted to you, Fatty. Lose some weight and I’ll do you!” but in a waaaay nicer way? And Wendy, not to sound rude, but can you please spare me from advice that suggests that I start cooking him healthy food, or asking him to go on walks with me — Not a chubby chaser

I’ll spare you the lame advice if you spare this guy the degradation of you trying to change him when he’s happy how he is. If he’s as sweet, considerate, fun, and “super confident” as you say, he won’t have any problem finding a woman who loves him as he is, extra pounds and all.

I am 27 years old and have been dating my boyfriend for a little over a year, and I couldn’t be more in love. The problem is that since I’ve been working full-time and going to school four nights a week and fostering a great relationship with my boyfriend, I feel really out of the loop with my group of friends from college. I feel anxious when we get together, like there are inside jokes that I’m not a part of and I have a sneaking feeling (which is probably 100% dead wrong, but I can’t shake it) that they sometimes hang out and don’t call me. If that were the case, it would break my heart, because I don’t ever want to seem unavailable to my friends, and I’d drop a night on the couch to hang out and get a quick drink to catch up. How do I go about shaking this feeling? Is there any way to resolve this without seeming like I’m begging for inclusion, since my friends might not have even noticed all of this? — Out of the loop

Instead of waiting for your friends to call you up and invite you out, take the initiative to organize a get-together. This will show that you are not only available for your friends, but you want to take an active role in remaining “in the loop.”

I’ve been seeing this guy for about eight months now. We hang out all the time, and text constantly when we’re not together. We both live at home since we’re still in school and we always hang out at my house. He’s gotten quite close with my family and has even met some of my extended family (not a big deal since we’re always hanging out at my house), but I have yet to meet anybody in his family or even go to his house. I used to often suggest that I go over there, or offer to pick him up if we were going out somewhere, but he always declined. He says that his mom is crazy and that is why he has never had me over there; I always reassure him and say that it doesn’t matter and that I can handle whatever craziness I come across. It’s starting to bother me a bit though. What can I do about this without seeming like I’m pressuring him to meet his family? — Unsure

Short of actually pressuring him to meet his family — which I don’t recommend — you can continue being a loving and supportive girlfriend and giving him a welcoming home to spend time with you in. You don’t know what kind of pain may lurk for him at his own home and the only way he’s going to open up to you about that part of his life is if you let him get there in his own time.

My boyfriend and I have been dating for about seven months now, and exclusively for three. Since the beginning, he’s had a habit of relaying to me any time he gets hit on by someone, or when he has a little crush on someone, etc. A month in, after coming back from a bar and bragging about how much flirting he did with a woman we know, I told him to cut the crap. He got pretty good at not doing that for a while, until a couple of our mutual female friends recently started coming on to him. I mean, I can’t blame him for loving the attention. I get hit on and asked out by other people all the time, but I would never tell him because it might make him worry. But he’s shown me flirty texts they’ve sent him, and still hangs out with them, even though he swears I’m the only one he wants to be with. I don’t want to stage a moratorium on him hanging out with other women, because that’s just fascist. But what is he getting at when he constantly has to flaunt that other women are interested in him? How do I even respond to something like that? — No Nonsense

You say this: “If you like the attention of other women so much, perhaps it’s time for us to end our relationship so you’re free to continue flirting and texting to your heart’s content. If that isn’t something you want, I suggest you find someone else to brag about all the attention you get because I’m seriously over it.”

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