Treating and Sitting and Smoking and Talking

There's no good way for me to say this without sounding like a bitch, so here: I want my boyfriend to pay for things. That's right, I said it. Our relationship is fairly new and things are going really well, but he keeps inviting me to dinner / lunch / drinks / coffee / whatever, picks me up and we go eat together and then he doesn't pay for me; just says "separate checks" and moves on. The first couple dates we went on, he paid. READ MORE

Gifts, Brolessness, and More Grad School From the Underworld

Is it weird / concerning when a guy primarily has only female friends? I've been casually seeing this guy who's pretty much only friends with women. He's admitted this being a "problem," saying things like, "I really need to find more guy friends." He's also a self-proclaimed feminist, and I think he's more sensitive than some other guys, which may be why he more often seeks female friendships. (Not to stereotype here.) READ MORE

Faking, Other Women, and the Top 50 Proposal Jokes

I've known a guy for about eight years now, and during that time I've pretty much always had feelings for him. We're now good friends, but it's hard because he has a girlfriend. However, he recently told me that he liked me and drunkenly tried to have sex with me. I would have gone for it, except I don't want to be the other woman. READ MORE

Four Men* and a Chest

(Ed. note: questions that have nothing to do with sex and/or relationships are always encouraged, too.) READ MORE

Mixed Signals, Mirrors, and Two Accidental May-Decembers

It's December 21 and I need to break up with my boyfriend. If I wait until after Christmas/New Years, I seem like a mooch who just wanted presents (I don't! I just don't want to ruin his holiday!), but if I do it before Christmas won't I just seem like a heartless bitch? I've needed to break up with my boyfriend since September ... ok, MAY, but I'm having a really difficult time with it! I really do care about him, he's a wonderful man, but I'm not in love with him and he does so many silly things that drive me batty. With other boyfriends I've just been brutally honest and called it a day — but I've been dating this guy for almost three years and he sees a future with me — I just don't see one with him. I guess I can figure out how to go about it on my own (though if you have any tips to soften the blow, please share! I've tried to break up with him three times already and he just doesn't get it). I'm really concerned about this delicate "it's the holidays" situation. ACK! PLEASE HELP! READ MORE

Old Pictures, Clownish Makeup, and the Unexplained Breakup

I have been in a wonderful relationship for about 10 months. My boyfriend is sweet, fashionable, loving, and basically everything you could ask for in a dude. (He bought me Prada sunglasses for my birthday without me even having to ask!) The sex is great, and I feel completely content with him, except for one thing… READ MORE

Snobs, Erotica Decoder Rings, and the New-Relationship Gift

I'm in a fairly new (five month) relationship with a man I'm bananas about. The holidays are coming up and already I'm agonizing over what to give him. I read in some women's magazine that if you give a sweater or other clothing that men associate you with their mothers, and that is not good. He loves watches, but I don't feel like we are exactly at the vintage Rolex stage yet. Though we are well past the "here's a book/album I think you would probably like" stage. READ MORE

Age Differences, Irrational Jealousy, and the Haircut

I'm a 52-year-old single female in an industry of youngs. I find that I'm invited to social events with people half my age and we have a blast. I go see their bands perform, we talk and hang out over FB and beers — they're just lovely people. But of course they're too young for me to make any moves on, even though there are a couple who appear to be circling me. READ MORE

Love, Bathrooms, and the Older Male Coworker

Hello, A Dude. I need help. I've been with my gentleman caller for eight months and I L-word him. I was going to tell him this several months ago, but then the day before I was planning on doing this we stumbled into a conversation where he said that he wouldn't be ready to say that for "a long time," so I backed off (I don't even know what he means by "a long time." A few months? A year?). I want to tell him how I feel, but he thinks it's too soon to say it (wtf?) even though by the way he acts and things he's done he obviously cares about me. We've met each other's parents (neither of us have ever done this), he took me with him across the country to his alma mater, we're going to Las Vegas together in a couple weeks, we're able to talk about months out assuming we're still going to be together, our rare disagreement is always settled quickly and easily by talking about it, etc. READ MORE

Questionably Tattooed Manchildren and New Uses for Old Jars

So, here's a question you guys probs get all the time, but I have to ask it because there is a crazy hamster in my brain who will just. not. get. off. the. wheel. READ MORE