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New Friends, Surprise Babies, and the "Rare Phenomenon"

1. I’ve been good friends with this dude for five years. I don’t want to be overly maternal or meddling, except: about five weeks ago, he was feeling mopey and went to a strip club after he got off work. He "struck up" a conversation with a young lady who was working there, and they discovered that they have a "lot in common!" Here is the sum of information he’s given me about her: READ MORE

Semi-Secret Affairs, Smanging, and the 88 Percent

Long story short, I finally grew a spine and broke up with my fiancé because he only added stress to my life, never gave any time to our relationship, etc. I moved out of our apartment, got drunk one night, and ended up hooking up with my boss. This situation seems to be turning into a very fulfilling relationship, except for one thing: I can't tell anyone about it, and this makes me wonder how serious it is. READ MORE

Lies, Kissing Biblically, and Translucent Officewear

So, I’ve been dating an AMAZING guy for the past seven months. He is loving and sweet and we’ve recently started talking like we have a long-term future together, which is exciting! I just have one concern that I think maybe is a big deal but maybe it’s only a big deal in my mind? Which is where you come in. READ MORE

Sixth Senses, Approachability, and the Penniless Nomad Actors

My fiancee just returned from a three-week tour. He's a musician and his band was on tour opening for a national act. We've been together for about two-and-a-half years, known each other for five. I'm also six months pregnant. He called me pretty much every day or night to check in and never went MIA. He's never cheated on me in the past (that I know of), but I just have this feeling in my gut he did this time. I don't know what it is, but I just can't shake the feeling he did. It's like a pregnant sixth sense is screaming at me 'he's a cheater!' and I can't shut it up. Our sex life hasn't exactly been the hottest thing since I've gotten further along, but it's not like he's in a sex Sahara. The thing that really makes struggle to believe him is that he told me the rest of the guys in his band all cheated on their wives. While I'm not totally shocked, I was surprised they ALL did but him. Doesn't the law of averages or something apply there? Like, I'm supposed to believe they all did but YOU didn't? And why would he tell me that? To throw me off? Wow, I sound (and feel) crazy, but please dude, help me out because I would love to believe him and move on. READ MORE

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