Are white lies a red flag?

Nice guy’s ‘working the system’ may be a deal-breaker for her

By Meredith Goldstein
Globe Staff / June 25, 2011

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Q. I am occasionally dating a guy, “Matt,’’ who is well-rounded, intelligent, ambitious, and caring. We are both in our early 30s. He is family-oriented and takes care of the people around him. He has been patiently pursuing me for quite a long time. He lives in a different city but he makes a point to come here to see me. Nothing hot and heavy yet, which is fine because I wanted to take it slow to understand if I really liked him just as a friend or as something more. We haven’t progressed to a relationship partly because we live in different cities, but mostly because of my lingering doubts about a few issues.

Matt is a great guy but has the tendency to push the boundaries as far as he can. He is fairly materialistic and success-oriented. He has told me a few anecdotes where he has told “white lies’’ or has omitted information in order to achieve a better status or situation. He does not do so in any way that would hurt another person, but to “work the system.’’ As he says, it is a dog-eat-dog world sometimes and to get ahead you can’t comply with every bureaucratic rule. And this approach is probably what makes him successful by a traditional definition. He is willing to take those small “harmless’’ risks.

After 30 years, I have come to realize that it is not my place to judge him, but rather to understand what I’m comfortable surrounding myself with. I am very risk averse. Not that I always follow every rule or never tell a white lie, but I tend to minimize the potential that something could go wrong, particularly for important things like my job or my house. I’ll lie and tell you that your outfit is cute or dinner was great, but don’t like to fib on a signed document. I’d rather be conservative and live moderately than live the high life and wonder if a negative consequence could pop up. I realize this trait makes me less fun-loving at times and I miss out on some opportunities in life.

This is the one issue with Matt that I’m trying to reconcile. Do you think I am making way too much out of the issue? My more adventurous friends find his white lies “funny’’ and my more strait-laced friends see it as a red flag.

He once jokingly told me that one of the reasons he likes me is because I am so grounded and that I am like his conscience. Shouldn’t he have his own conscience?


A. This is a big yellow flag. You have to trust your gut, and your gut doesn’t like how this guy makes important decisions.

We all tell tiny lies and “work the system’’ to some point, and what’s OK for one person seems like a crime to someone else. I once saw a friend of mine ring up avocados as less-expensive oranges on the self checkout line at a grocery store. In my mind, it was full-on shoplifting. I was convinced that we were going to be locked up for a massive fruit heist. But on Saturday, at the airport, I told the people at customs that I didn’t buy anything in Ireland even though my suitcase contained Irish chocolate and stuffed animals for my friends’ kids. I just didn’t want to wait in a long line. It wasn’t a big deal to me, but I’m sure it would have been to someone else.

My point is that in any relationship we wind up watching a partner do something that makes us uncomfortable. That’s normal. But (and this is a big but) it shouldn’t happen frequently.

It sounds like you’re questioning Matt’s decisions all of the time and that you’re uncomfortable with the way he makes choices that would affect your life if you lived with him.

It doesn’t help matters that he’s far away. If you lived in the same city you’d have a better understanding of his boundaries and whether you can make peace with them.

Unless he’s going to live closer to you and show you what he’s really made of, you have to trust what your gut knows now. You can’t spend your life being uneasy and hoping that your partner doesn’t do something that makes you want to hide under your bed.

You’re right — it’s not your job to judge. It is your job to be honest about what you can put up with. And you can’t keep stringing him (or yourself) along if you can’t deal with his ethics.



Yeah. It was little white lies such as this that contributed to the mortgage collapse. Ask yourself this: Would you want to teach your (theoretical, future) children to act the way he does? Could you justify his behavior to them if they asked?


Seriously, I don’t think you should have to ask if your unwillingness to forge a legal document makes you less “fun-loving.’’ You gotta draw the line somewhere, criminal activity seems to be a good start. PIERCE-PATCHETT

You’re a fool if you think he lies only in matters involving money. He’s fully capable of lying in matters of the heart too. Why would you even consider a future with a man who is clearly is capable of fraud and possibly capable of adultery?!!!!! Walk away now, while you can. Scratch that — run like hell now, while you can.


Some of you need to get your head out of the sand. Business in today’s America requires working the system. The regulatory mechanisms that are set up practically beg you to lie as there is no way to fully comply with all those rules.


So let me get this straight, anyone who has told a lie in their life automatically gets labeled a liar? Am I on “Reading Rainbow’’? Have I been transported into a Nathaniel Hawthorne book?


I’ve cheated on taxes, but never on women. Can’t assume that they are associated. That being said, you don’t want to cast your lot with someone who puts you at risk beyond your comfort zone. What might bother me more is simply being associated with someone whose values I don’t share. RICKYGR

Oh Meredith, beloved, large-hearted, and head-headed advisor to the lovelorn, I beg to differ with you. This man is not “a big yellow flag.’’ He is a red flag. KAZARINA

Edited and reprinted from Meredith Goldstein can be reached at She chats online Wednesday at 1 p.m.