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Had to Get Away

Sometimes it's time to take a break

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Dear readers: This is the final week of my summer vacation — but you've been getting a new column every week I've been gone, all of them written by a Dan Savage, none of them written by me.

Our final guest Dan Savage is an independent designer, illustrator, and animation director based in Brooklyn, New York. He created Yule Log 2.0 (watchyulelog.com), a collaborative art project where animators around the world reimagine the famous Yule log fireplace. He has worked with the New York Times, Herman Miller, and Google, he's taught design and animation, and he's won a bunch of design industry awards you probably haven't heard of.

I'm a 41-year-old straight woman who stayed a virgin way longer than I should have (thank you, church and cultural slut shaming). I wasn't 100 percent "good," i.e., I was one of those "not PIV = not really sex" girls, so I indulged in outercourse and other "cheats." When I finally realized that "not until marriage" wasn't working for me and did the real thing, I discovered I loved it. Go me, right? Unfortunately, I'm not good at dating, so I usually go a long time between relationships. The relationship I'm in now is the first one I've had in two years. "Guy" is nice to me — calls me beautiful, sticks up for me, comes to watch me play with a community orchestra (my own family and friends don't even come to my shows). But we don't have much in common (hobbies, political outlook, religious beliefs) and sometimes our conversations feel labored. But that's okay, right? At least I'm getting my sexual needs met, right? Well, no. Every single time we've tried to have sex, Guy either can't get hard or stays hard for only a few minutes. I've tried going down on him, using my hands, different positions—nothing works. He's never had an orgasm with me. We don't even kiss that much. I don't say anything because I don't want to hurt his feelings and because I'm really grateful to him for wanting to be with me and being nice to me. He says sorry and that he's asked the doctor about it, but we don't get anywhere. It feels lonelier than when I was single. To be blunt, I don't want to date him anymore. But I feel too guilty to break up with him. He really cares about me, and he didn't do anything wrong. We've dated for four months, and I don't know if I'm giving up too soon. Where would I be if previous boyfriends had ditched me for being inexperienced instead of showing me the ropes? Don't I owe Guy the same thing?

Too Down To Be Witty

First off, I think a long time between relationships is good. I also think not having things in common can be okay if you create new hobbies and experiences you can share. Having said that, TDTBW, four months is plenty of time to know if it's working. He sounds super boring. The sooner you break it off with him the better. You don't want to hurt him any more than you have to, especially if he's really into you, and the longer you draw it out, the more it's going to hurt. No amount of "training" is going to get this dude hard. The only rope being shown here is his flaccid ding-dong. It doesn't seem like you even want to be his friend if you broke up. I wouldn't feel guilty at all about dumping him.

My girl and I are both 26, and we opened up our marriage. Now I've got a girlfriend with whom I am getting to have some of the kinky fun that was lacking at home. Here is my question: Things are really casual between me and this new girl. I want to do some pegging, but I don't know who should buy the strap-on? Me, because it's my ass and my idea? Or her, because she would wear it and would also think it was super hot? Should I buy the dildo and she buys the harness? Going halfsies on the whole rig? What is the equitable way of doing this?

Purchasing Erotic Gear Good Etiquette, Dan?

You're 26 years old, PEGGED, buy the damn thing. How much could it possibly cost? I know if I were in your situation, I would want full control over what goes up my ass. If she owns it, would she use it while you weren't around? With strangers? No thanks. Plus if you split the cost, who gets to keep it when you break up? Just buy it and enjoy. If you struggle with picking it out, might I suggest starting small?

Follow Daniel Savage on Twitter at @somethingsavage.

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