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Thank you for your wisdom on the subject of finding and keeping a man. I am one of those women who has been unknowingly making men feel bad about themselves forever.  I met a great man a year ago and he treats me really well (has good character). I have realized recently that I don’t feel I can totally trust him, as he is a people pleaser.

I have realized recently that I don’t feel I can totally trust him, as he is a people pleaser.

I don’t think he’s intentionally untrustworthy or lies, but his main motivation is to keep people happy, including me. This is great on the one hand, but on the other hand, he tells small white lies, has trouble opening up and communicating his feelings, and withholds information at the risk of upsetting me. I have trust issues from past relationships and finding it hard to move emotionally forward with this guy. Can you please help?

Many thanks,
Sunny

Your letter reminds me of a predicament faced by a client named Anne in New York City. She was in her early forties, wanted to start a family, and was dating a nice middle-aged divorced man who treated her like gold. However, his ex-wife did a number on him and brought out a lot of his insecurities, which still surfaced despite his solid relationship with Anne.

I remember her asking me virtually the same question you did — and I remember being challenged by it. See, I’d like to think of lying as a purely black and white issue, since, for me, personally, it is. But it’s not my job to impose my values on everyone; rather, it’s to understand how real people actually work in real life. Case in point: a 53-year-old woman is tempted to lie about her age and make herself 49 on Match so she can be seen by more men via the dating site’s algorithm. Is she a liar? Unethical? Probably lying about something bigger? Not in my book. To me, she’s simply insecure that telling the truth will sabotage her ability to meet enough desirable men. So while I don’t encourage lying — I think it’s a corrosive slippery slope –   I try to avoid being judgmental about these type of white lies without greater context. It sounds to me, Sunny, like you do as well.

With Anne, I encouraged her to lean into the relationship even more. If her guy’s ex-wife was supremely critical and made him feel he had to lie to keep the peace, the way to get him to be more authentic was by being more supportive and accepting. Sure enough, this worked like a charm. Anne let him know he was safe, to tell the truth, and, in return, she got a more confident and honest man. They later got married and are, to the best of my knowledge, still together.

Your situation is slightly different because you added issues of opening up, communication, and past baggage on top of the little white lies. Each of those individually is a yellow flag, which, collectively, adds up to a potential red flag for your relationship.

Each of those individually is a yellow flag, which, collectively, adds up to a potential red flag for your relationship.

I suppose you can make the argument that all of these things are intertwined — most likely, they are. But then you’d have to make the argument that it’s a wise idea to build the foundation of your life on someone you don’t totally trust. Objectively, it’s not.

There are lots of good people who do bad things. You don’t have to marry them.

My recommendation is to confront him with your feelings in a tenderhearted but honest way. You’ve got a small laundry list of trust issues with him that you need to iron out in order for the relationship to continue to grow. If he wants to start now by owning up to them and making them right, you have a fighting chance to succeed. And if despite your efforts to give him the benefit of the doubt, you still don’t feel comfortable, you are well within your rights — and highly encouraged — to find a man whose character is impeccable. Life is hard enough. You can’t afford to doubt the person who is closest to you.