I recently asked a woman out to dinner on a first date. I normally pay for the first several dates, especially if I've done the inviting. We went to Prospect, which I thought was classy and upscale without being too over-the-top (e.g. Gary Danko, etc.). But after cocktails, starters, entrees, wine, and dessert, it turned out to be the most expensive first date I'd ever been on. She offered to split the bill when it came, and I succumbed and let her. But then I called for a second date and I'm getting crickets. Mistake?
I'm in my mid-20s and recently hit it off with a 30-something guy at a bar. He's finalizing a divorce and has a couple of kids; I've been contemplating a break from my three-year boyfriend. He advised me to leave while I'm young, as he knew his marriage was a mistake from the beginning. We've been texting, hanging out, and we've kissed. He's enjoying the single life and acts like a guy in his 20s: last-minute plans, indecisiveness. But sometimes I think he wants more than friendship or booty because he'll act chivalrous, hold my hand, and say certain things. For my part, I don't have the heart/strength to break it off with my boyfriend right now, yet I'm flirting with this man because I've never really dated much. I've either been totally single or in a relationship.
My boyfriend and I have been dating for almost a year and a half and although we have really intimate talks, I feel like I don't know him. He's told me he loves me, confessed he's cheated on every girlfriend he's ever had, but says he feel differently about me. He's thoughtful, buys me gifts, and plans romantic weekends, but I often can't get a hold of him during the week. I’ll call and leave a message and then get a short text response an hour or two later. When we're together, I feel like everything is fine, but when we're apart, I'm not sure. I don't know how much of my suspicion that he may be seeing someone else is a projection and how much is common sense.
A couple of years ago I hooked up with and dated a cute, sexy, and smart girl who seemed really cool at first but over time started some nasty fights with me, so I stopped going out with her. Recently I heard that a friend of mine is dating her and it sounds serious. I’m torn about telling him that I dated her. On the one hand it’s none of my business whom he dates, but on the other what do I say if he introduces me to her? I’m also worried because she might drop my name during a fight with him in a way that would make it hard for he and I to remain friends.
As a gay man, I’ve noticed that a lot of the younger guys have started bringing their gal pals along to clubs. At Trigger some nights, there are as many straight girls as gay guys. That’s fine, but it can also be a “c*ck block.” Guys don’t hook up for fear of abandoning their pals. Also, more straight guys have been showing up, swift on the tail of the cute girls. Mistaking a straight guy for gay is a real mood killer. What to do?
From a man’s point of view, how long should I stay at his place after a casual hookup or one-night stand? What goes through his head if I get up and go right away versus wait an hour or so versus leave in the morning? Does it actually matter?
My girlfriend and I recently got engaged, and all my guy friends—especially the married ones with kids—are talking about throwing me a bachelor party in Vegas. This is my second marriage, and I feel like it’s inappropriate to throw a (second) big bachelor party. What do you think?
I’ve been married two years and my husband always “forgets” to wear his wedding ring. He takes it off to exercise or cook and then just leaves it off. He admits he doesn’t like wearing it because he isn’t a “jewelry guy,” and it bugs his finger. Naturally, I don’t like this one little bit. What do I do?
I’ve been dating a girl, and it’s starting to get serious, but I have long-term doubts because— here goes—she’s had too many lovers. I expect a woman to have had 15 or 20 or maybe even 25 lovers by the time she reaches her mid-30s, but this girl has had twice that, and while my rational side understands the math, some part of my lower brain finds it hard to trust her.
I’ve been dating my boyfriend for over two years and living with him for one. He’s going to grad school in the fall and he wants to try a long-distance relationship. At 30, I don’t know if I’m willing to wait another two years. How can a long-distance relationship work after we’ve lived together? How can I control myself so that I don’t turn into a jealous girlfriend who’s constantly worrying that her man is looking at 20-year-old undergrads? He tells me he isn’t ready to propose and needs to finish school. But it doesn’t seem fair to wait around at my age.
—30 and Ready in SoMa