Black and white, right and wrong, cut and dried. I know how tempting it is to look for a “rule” or a quick answer in dating. Leave or stay? Unmatch or meet? But most things in life are not answered so simply. This week, we have several dating questions looking for a back-and-white answer … and I’m here to show the shades of gray.

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Dear Anna,

I’ve been dating my boyfriend for about four months, and things have been going really well — or at least I thought they were. He’s always been really thoughtful over text, sending me these sweet, articulate messages about how he’s feeling or why he appreciates me. I’m not the most eloquent person, so I’ve always been a ...Read more

Dear Anna,

I’m 34 and recently got back into dating after a five-year relationship ended about a year ago. I took time to work on myself, went to therapy, and I’m finally ready to put myself out there again. The problem? I’ve completely lost the ability to tell if someone is actually interested in me. I’ve been on maybe eight or nine ...Read more

I recently had someone reach out to me about a dating dilemma: The man she was “dating exclusively” (her words) told her he was no longer on apps. However, a friend spotted his profile, which was not only “active now,” but updated. When this person approached the man about it, he claimed that the app kept his dating profile active for �...Read more

Dear Anna,

I’m 28 and for the past few years, I’ve been fully committed to the casual hookup lifestyle. I’m bisexual and I’ve had a string of no-strings-attached situationships with people I met on apps — probably a dozen or so in the last two years alone. I was totally fine with it. I wasn’t looking for anything serious, and ...Read more

A male client of mine went on 12 dates with a woman over a few months. (For what it’s worth, if you’re still counting the number of dates at this point, I do have to wonder why.) Regardless, my client is looking for a long-term relationship and he wasn’t sure how this woman felt about that. I encouraged him to tell her what he’s looking ...Read more

Dear Anna,

When my husband and I got engaged in our 20s, we were barely scraping by. He proposed without a ring, and we got married not long after with a small, low-key ceremony — no bands, no big gestures, just the two of us building a life together. At the time, it felt completely right. Fifteen years and a couple of kids later, things look...Read more

Another day, another batch of dating questions — some about losing hope in finding a partner, some about defining the relationship, and some about date planning. Perhaps one will especially resonate with you.

Q: We’ve been dating for three months. I’m ready to define the relationship. I'm afraid he might not be ready yet. Bring it up or ...Read more

MINNEAPOLIS -- Five Saturday weddings featured something old, something new, something borrowed and something red. Make that something “read,” since the weddings happened at Minneapolis Central Library.

The weddings took place in 15-minute intervals in Pohlad Hall, with receptions in a nearby meeting room. Each couple were allotted 25 ...Read more