Amy Alkon

I’m a guy who hates fake boobs. I’ve dumped women I really liked upon discovering they have them. Total dealbreaker for me. However, I obviously can’t just ask whether a woman has them. What should I do? I don’t want to waste my time or hers. — Real Deal Right. Not exactly a first-date question: […]

I’m a 35-year-old masculine gay man. I’ve had relationships with (masculine) gay men, but I’m often attracted to masculine straight men. I’m not looking to “turn” them, and I’m ready for a relationship, so I’m concerned that I’m so frequently attracted to men who won’t be interested in me. What is this about? Do I […]

I have this disturbing pattern. I’ve dated three different guys, each of whom said he didn’t want to get married, wasn’t ready, whatever. But then, the next girl they met … BAM! Walking down the aisle. Why am I marriage boot camp but never the one the guy marries?  – Aisle Seat Although our mind’s […]

A dear friend who’s also a co-worker just went through a breakup with her girlfriend, and she’s devastated. I don’t know what to tell her. I’ve tried everything: You dodged a bullet; it’s a blessing in disguise; you’re better off without her; you should get back out there. Everything I say seems to be wrong, and […]

I’m a 40-year-old man who can’t seem to keep a relationship going for more than a year. There’s never bitter fighting or betrayal. I just gradually lose interest. I can’t blame my girlfriends – most of whom are pretty exciting people. I’m the problem, but why? And can I change? – Frustrated Ever gotten new carpeting? […]

I got in an argument with my boyfriend about the reason not to have sex outside our relationship. He said he wouldn’t do it because he wouldn’t want to hurt me. I said he shouldn’t want to be with anybody else, but he said that’s just not realistic for guys. Are men really just these […]

I’m a woman in my 30s. I love parties and talking to people, and thank God, because I attend networking events for work. My boyfriend, on the other hand, is an introvert, hates talking to strangers and loathes “shindigs.” How do we balance my longing to go to parties with his desire to stay home? – […]

I’m a man in my mid-30s, and I’m dating a woman I really love. We match each other on so many levels, and I thought we had a really great thing. But recently, she seems to want more than I can give. Specifically, she’s prodding me to say “I love you” repeatedly throughout the day, […]

I love my boyfriend; however, I feel bad that he never buys me presents. He did when we were dating, and he buys himself extravagant stuff. But he got me nothing for my birthday and only some trinkets for Christmas because I made a stink. When I’ve brought up the gifts issue, he’s implied that […]

I’m extremely insecure about my looks, though objectively I know I’m pretty. I constantly ask my boyfriend for reassurance. He gives it to me but feels bad that I feel this way. Now I’m worrying that I’m making such a good case for what’s wrong with me that he’ll start believing me. Possible? – Bag […]

Nobody expects a free meal from a restaurant. So what’s with wedding guests who think it’s acceptable to give no gift or just $100 from two people? My understanding is that you are supposed to “cover your plate” – the cost of your meal (at least $100 per person). If you can’t, you shouldn’t attend. […]

I’m in love with my married female co-worker. I’m married and have no intention of leaving my wife, and I doubt she’d leave her husband, even if she shared my feelings. I love how caring and kind my co-worker is – how she understands that you show love through action. I do this by often […]