Should I Stay or Should I Go?


Welcome to our new weekly blog of half-truths and educated guesses on love, sex and relationships in SF. Here's who's dishing the advice:


He is a novelist living in SF who’s had one marriage, two live-in relationships, 10 girlfriends and a very wise therapist.

She is an SF health journalist who’s been married, single, communal, and bi-curious, and has studied tantra and orgasm—for research purposes, of course.

Q: I’m 28, have been dating a great guy for four and a half years, and we’ve talked about marriage at some point in the future. We laugh, hike, camp and have a lot of fun. I’ve been in two long relationships, and recently have been having bursts of desire to do things I’ve never done, like date, have a fling, live by myself. But I fear throwing away a relationship that could last a lifetime. What do you think?

He Said: Quite a dilemma: Stay connected with a great guy or unhook and slip into the unpredictable stream of spawning singles.

One thing’s for sure: You should never stay in a relationship out of fear or guilt. It sounds as though you’ve been good for each other, and if it’s time to move on, that’s no one’s fault. It also sounds like you are both able to build long-term relationships—a good sign that you can do so again with a new partner.

Bottom line: Wait a few months and see if these recent feelings pass or get stronger. During this period, ask yourself if you’d want to stay with your boyfriend if you were sure you could find someone just as compatible in the future. If the answer to that question is no, then tell him you need some time alone. If it’s yes, then stay.

But don’t wait more than six months to make a decision. Like graduate school, dilemmas are snooze bars on the alarm clock of life. While it’s tempting to keep slapping them and stay half asleep, you don’t want to wake up some afternoon and wonder where the day went.

She Said: I’ve been there: at 25, at 36, and believe it or not, again in my 40s. And what I’ve learned is: If you have a deep desire to live alone, or date, or have a few wild flings, chances are these feelings are not going to disappear. I agree with The Man that you should wait a little bit—I’d say a month at most—before deciding whether these are fleeting daydreams or real desires. Thirty days from now, if you still want to do any of these things, tell your boyfriend, and then do them.

What strikes me most in your letter is this: “We laugh, hike, camp and have a lot of fun.” You can do all of that with a great friend, a sibling, a parent—anyone really. But this is your potential husband, and you are trying to sum up your relationship in one sentence. If that sentence went something like, “He feels like a soul mate, he challenges me, and I’m wild for him” or “He’s brilliant, sexy, and the best mate I could imagine,” then my answer would be more conservative. But, going for the most part on my feminine intuition here, I think this man’s main attraction may be that he feels safe to you. Safety is great—I’m a huge fan of it-—but it’s not everything. Something’s itching in you, and I personally don’t think it will go away.

I also agree with The Man that this is a dilemma; it boils down to a choice between the known and the unknown, between security and risk. These two poles will reappear often (the creative low-paying job vs. the more boring lucrative one, the scary trek in the mountains vs. the relaxing beach vacation). There will be many times you’ll want to choose on the side of security and routine, and these instances will increase as you age. So I say if you’re unsure, then lean toward the adventurous option. Do it now, while you’re young. Time is on your side. You have at least a decade to get married—more if you don’t want to have kids.

Confused? Heartbroken? Curious? Send your questions to and we might just answer them here. Have thoughts about this post? We want to hear 'em! Comment below.

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