He cheats the system

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Update news at 11:22 a.m.: The letter writer has an update on comment pg. 15.

Dear Meredith,

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 adverse. 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 then 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 straight 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???

– Little White Lies, Boston

This is a big yellow flag, LWL. 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" at 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 check-out line at a grocery store. That killed me. 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.

Readers? Is there any hope here? Is she being a prude? Does anyone out there have to live with their partner's unethical choices? Is distance an issue here? Discuss.

– Meredith