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Leslie -
Good question - How long are we to please a weaker brother/sister? The more we please them just to avoid hurting them, I think we do damage to their possibility to come to terms with the freedom that is theirs.
As we all know, each person/situation is different. Though there are some that 'flaunt' their freedom, we can also probably assume their are some that 'flaunt' their personal convictions. I have a testimony or two in my own life of flaunting my convictions in my more legalistic days. And I am glad for my 'spiritual father' having grace enough to be patient but also the willingness to challenge me. I distinctly remember him saying one day, 'Scott, I just need to take you fishin' out on the lake and get you drunk.' :) He wasn't being literal, he was making a point.
Anyways, there is a time and place in which appeasing the 'weaker' person's convictions will get old and stale, meaning that there is obviously no life being breathed every time certain issues are discussed. If it is someone we very rarely see, or meet once, I wouldn't spend the energy 'convincing', since we don't already have an open door into their life. But if it is those we regularly relate to, and even have a mentoring role over, we will, at the right time, need to address the legalistic convictions. And it isn't all for the sake of them being able to go out and have a beer (though that might be helpful), but it is all about them coming into the full freedom that Christ provides in our lives - from sin, from perfectionism, and other such evil roots.
One final practical thing to consider is that, if we who take part in things that others might consider 'sinful' (certain movies, beer, certain music, etc), but we show that we are truly and authentically seeking God, then I believe that will have an impact on seeing them come through. I have seen that with my own friends. They start to question - 'I thought drinking beer was a sin. But here is my friend whom I love and I know that they are pursuing God with their life, but they are also enjoying a beer. Maybe it isn't a sin. Maybe I have just built up a legalistic belief.'
Something of that sort.
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