I see legalism during Lent sometimes, and I think it can be problematic. Lent should not be about proving to yourself (and definitely not proving to other people) how strong your will is and how disciplined you are. It is about clearing away attachments so that we can more completely attach ourselves to God. With that being said, I offer some tips for Lent
1. Don't tell people what you are giving up for Lent.
2. Don't ask people what they are giving up for Lent.
Don't try to guess what someone gave up for Lent either
(Dave: "Bill, you want some coffee?"
Bill: "No thanks."
Dave: "What, did you give up coffee for Lent?" - don't be Dave!)
3. If someone breaks #1 or #2 with you, don't correct them (although if you are giving up a few things, you can just mention one thing you've given up to satisfy their curiosity).
4. If someone offers you something that you have given up for Lent, I advise proceeding in one of two ways, depending on the situation
a. If it is a situation where you can casually brush off the offer without drawing attention to it, then just decline the offer
(example: "Dave, I'm going to the concession stand...do you want anything?"
Dave: "No I'm fine."
Dave does not have to say "No, I gave up candy and snacks for Lent.")
b. If it is a situation where you are with a small group of people, or you are at someone's house for dinner or something like that, and they offer you dessert or something, just take it and don't tell them "Sorry, I gave that up for Lent." If someone gives up TV but the whole family is watching TV, don't go sit in the other room, just watch TV and be with the family.
5. Don't replace what you are giving up with some other thing that you are attached to
6. Take advantage of the detachment to do something positive like prayer and/or doing something to help the poor.
7. If you normally celebrate Sundays and Solemnities during the year with a spirit of feasting, then continue to celebrate those days during Lent. If that involves breaking something that you're fasting from, then break your fast. However, if you don't celebrate Sundays or Solemnities, then don't break whatever you are fasting from during Lent.
8. Try giving up several things up for Lent, but maybe phase them in over time like the Orthodox. For the Orthodox, Lent gets gradually more challenging. I have tried making Lent more challenging as it progresses, and that has been really fruitful!
9. It is also good to DO something for Lent; to add a spiritual practice to your daily routine in addition to giving something up. Perhaps praying a daily rosary or praying every morning when you get up.
The important thing is to realize that Lent is a time to strip away some attachments and spend time growing closer to Christ not crossing the finish line of Easter 46 days from now with your Lenten promises unbroken at all costs.
Lent is made for man, not man for Lent!