I’m looking for an honest woman

It's all in the delivery ...

Mere, here is a question that I struggle with as a man. I have just recently learned that women friends lie to each other regularly and withhold feelings from one another if they feel that the other might be upset by their own feelings, truth, or opinion. They think that it is loving to save them from their own negative feelings. It is apparently an exception that one might be honest with the other and share any truth about feelings that they have with the other if they perceive that the other might get upset. Men value honesty, clarity, and directness in their friendships.

In the past couple of relationships I've had, women seemingly wanted to be treated in the same manner they would by their friends. For example, my last relationship ended because my girlfriend had fear about paying a bill. After the crisis passed a couple weeks later, I told her that I was concerned about her deteriorating financial situation (partially reflecting her own fear back to her) and asked her about what priorities she had in her life. Because I was aware of her situation, I had been paying for the vast majority of dating expenses and helped her with other tasks so that she wouldn't be further financially burdened. She blamed me for causing her to go into a deep sense of fear and told me that I shouldn't have expressed my feelings or concern. When I told her that I wouldn't accept blame for her feelings, she basically told me that I needed to change. I've always put what is best for the relationship first. Obviously, allowing her to control me would be unhealthy for our relationship and for me. Sadly that happened in my previous marriage of over 20 years.
I believe that you can only have an authentic and intimate relationship if non-harmful self-expression is encouraged. Non-harmful self-disclosure might be something like "I feel sad about ...," "I feel worried about ...," without any criticism or blame. Since a healthy relationship was not modeled for me by my parents, I am following what relationship experts consistently advise couples to have a loving, healthy, and intimate relationship.

I don't want to dwell in the past. I am ready to move on. So now as I begin dating again, what qualities do you think I should look for in a woman that would suggest that they can take responsibility for their feelings and invite their partner to be authentic, vulnerable, and intimate? Or is that impossible and you can only tell once the power struggle in a relationship commences six-nine months down the road?

– Looking for a Self-Responsible Woman, Cambridge

LDASRW, we're going to have to take a big time-out here.

All women are not created equal. Some women are afraid of honesty. Some women are so honest they'll make you cry. Same goes for men. Please, please, please do not generalize when it comes to gender. And please, please, please do not make decisions about "what women do" based on one ex-wife and an ex-girlfriend who's embarrassed about debt. Really.

Honesty is all about intent and delivery. You're right -- relationship experts love open communication, but they also love empathy. "I'm concerned you don't pay bills. Really, what's up with your priorities?" sounds different than, "You seem stressed about your finances. I'm sort of good at managing money. Can I sit down, as your friend, and work through it with you?" And yes, you're allowed to add, "I'm asking, partly because if I keep paying for everything, I'll be skipping bills, too. Can we have one of those awkward talks about cash flow?" (Said with a sheepish grin on your face, not a look of judgment.)

It's not about lying. It's about presenting information so that the truth doesn't obscure itself by clouding the recipient's brain with more anxiety.

My advice is to look for someone you really respect -- someone you want to befriend, not just date. In fact, I recommend seeking out some women friends (this will help you stop generalizing) and perhaps one of them will turn into something more. I think it'd be great for you to date someone you already know well.

If you already have some close female friends, ask them what they think is going on. Something tells me you'll be startled by their honesty.

Readers? What happens when we generalize? Are his generalizations accurate at all? Could this be his delivery? Is this about his ex-wife? Should he start by finding more female friends? How should he do that? Do I look fat in this dress? Be honest.

– Meredith