Dear Wendy: “My Boyfriend’s A Bore”

About six months ago, I met this guy, Alex, who I thought was perfect. He is about to graduate law school, he is unbelievably kind, respectful and empathetic, and also the sex is great. But I have slowly begun to realize that Alex is very safe — meaning he’s not spontaneous and not very funny – he’s sort of boring, really. Right around the time that I was realizing Alex’s true colors, I went on a trip to my childhood best friend Harry’s cabin in the woods. We ended up having so much fun and for the first time since we’ve been friends I’ve started to have feelings for him. Nothing romantic happened between Harry and me, but I’m not sure what I should do with my feelings. I feel very guilty being in a relationship with one person when I can’t stop thinking of my best friend. Should I tell both men how I’m feeling? I’m worried that if I tell Harry how I feel that I will lose his friendship, or that it will change things between us. And I’m worried that if I tell Alex he will resent me and think that I was playing a game with him. Please help me make sense of my mixed up emotions. — Between Two Men

What you need to do here is look at both relationships independent of each other. Whether you say anything to Harry or not — and we’ll get to that in a minute — you need to end things with Alex. If you’re only six months in and already feeling like he’s boring, too safe, and not very funny, there’s probably nowhere for this relationship to go but down. You don’t need to tell Alex there’s some other guy who might or might not be in the picture. Simply explain to him that as much as you like him, your feelings have changed and you no longer desire a relationship with him. You’re not “playing a game” with him. It’s called dating and this is what happens sometimes — you like someone at first and as time goes on, you either drift apart, meet someone you like better, or realize as you get to know the other person that he isn’t right for you after all. You don’t owe Alex some long drawn-out explanation beyond telling him you’re just not feeling it anymore. But you do owe him the courtesy of letting him know right away where he stands. Breaking up with someone is never fun, but leading him on because you don’t want to be the “bad guy” actually makes you just that. So, step up and do what you need to do.

As for Harry, I say go for it. Sure, there’s potential that you could lose your friendship, I guess, but if you have been friends since you were children, one would hope it would take more than a confession of a crush to fracture your bonds forever. And with any luck, Harry feels the same way you do and you can begin building a romantic relationship on the strong foundation of your long-time friendship. What could be better than that?

My sister is a mid-30s single mom who is beautiful, inside and out. She has struggled with her weight for a long time, but in the past few years, her weight has ballooned to dangerously high numbers. Last year, a doctor told her that her cholesterol and blood sugar levels were very unhealthy and unless she dieted and exercised, she would have to begin taking prescription medication to get things under control or risk having a heart attack or developing diabetes (the latter of which runs in my family). She was very upset after this appointment and vowed to get healthy, and even saw great results, losing weight on a weekly basis.

Flash forward to today, and my sister has gained even more weight. She is flat-out obese. She never exercises, she skips meals and eats junk. Worse yet, I fear that she has no desire to even lose weight. She’s started dating again, but has found that some guys like larger women, which my other siblings, mother and I worry is just reinforcing her habits even more. She’s a serious workaholic with lots of stressers, too, and I am very worried that she’s going to have a heart attack any day now. My family agrees that she needs to start putting herself, and her kids, first. But, how do we even start this conversation with her? Part of the problem is that the rest of my family is slim and active, choosing to eat healthy foods and to exercise. No one wants to come off as the thin, judgmental mediator, especially because she’s been through some rough patches in the last few years, but I am so worried for her and so afraid that something will happen and her young children will be left without a mom at a very young age. — Concerned Sister

Without going into personal details, I so know where you are coming from. I’ve been in your shoes; I know the worry you feel and I understand more than you can imagine the delicate balance of showing concern without hurting feelings, or worse, igniting jealousy or creating bad blood between you and a loved one. And make no bones about it: this is a slippery slope and one you have to navigate as gracefully as you can. As noble as it may be to want to help your sister — to find just the right words to pull her from her self-destruction and to save her children from a life with a sick mother — or, God forbid, no mother at all — experience has taught me that it’s best to err on the side of silence — or near silence — rather than risk saying the wrong thing and alienating oneself from a loved one who needs you.

That doesn’t mean you can’t show support in your silence, though. You absolutely can. Because, look, it’s not like your sister doesn’t know she’s obese. It’s not like she isn’t aware she’s at risk for a bunch of health problems and that she’s setting a terrible example for her children. So, she doesn’t need you to point those things out to her. But what she could use is your emotional support, unconditional love, and your reservation of judgment. So, tell her you love her. Tell her you want only health and happiness for her and if there’s anything at all you can do to help her achieve those things, to let you know. Let her know what you value about her, what you’ve gained and learned by being her sister. Ask her for support and advice when you can use it so the playing field is a bit more even and she doesn’t feel like the odd woman out whom everyone else just feels sorry for.

Whatever you do, don’t talk about weight unless she brings it up. It’s there all the time like the elephant in the room and it really doesn’t need to be acknowledged because everyone already knows it exists. Everyone sees it all the time. Instead, ask her if she wants advice and help to get in shape. Explain what you are able and willing to do to help, from teaching her how to cook healthy meals to babysitting her kids while she goes to the gym. And then drop it — and tell her you’re going to drop it. Let her know you are there as a resource if and when she decides she wants your help, but you will not mention it again unless she does. Because if she’s going to ask you for help, it has to be on her terms and it has to be when she’s ready. If there’s one thing I’ve learned from experiencing a similar situation, you can’t help unless/until the other person is open and ready for your help.

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]”}.