Dear Emuna,

Every year at this time I feel so guilty about my past behaviors. Whatever vows and resolutions I make, I end up breaking. I always feel like I’m back at square one, which only makes me feel more depressed and guilty. How do I break this vicious cycle?

-- Obsessing

Dear Obsessing,

Since you are always back at square one, you clearly need a different strategy! Let’s start with losing the guilt. Not only is guilt really not a Jewish idea, it is actually anathema to Torah. We don’t believe in sitting around beating ourselves up for our mistakes (despite that chest-pounding on Yom Kippur). It’s counterproductive. It creates the illusion of action. We believe in healthy regret that spurs action. You made a mistake – do something about it. Confess your misdeeds. Express contrition. Repent. Make a commitment not to repeat them. And make a plan. A realistic plan.

Just like an alcoholic needs to change his route home from work to avoid the neighborhood bar, we need to change our behaviors and habits as well. Don’t go to the book club where the real pastime is gossip if you’re working on not speaking badly about others. Don’t ask questions that have led to gossip in the past. Make a commitment to spend one particular hour a day free of gossip.

Don’t walk past the bakery if you’re trying to lose weight. Don’t bake your favorite dessert. Do join weight watchers. We need to think strategically and plan our attack from all angles.

Don’t plan dinner for 6 if you can’t get home before 5:45. Don’t make something that has to be prepared immediately before eating. Plan your menus thoughtfully and carefully with everyone’s schedules and dietary needs in mind.

Some of these examples are trivial and some are serious, but you get the picture. If you make a plan that has simple, practical steps you have a much greater chance of success. Write it down. Evaluate daily to see how you’re doing. Ask for the Almighty’s help. And pray for a guilt-free, growth-filled new year.

-- Emuna

Dear Emuna,

How do I know when I’m ready to date?

-- Single Girl

Dear Young Girl,

This topic may be better suited to Rosie Einhorn and Sherry Zimmerman, but since it came to me I will have the presumption to make a few suggestions.

1. Are your friends all dating? On the one hand, this may be confusing. The fact that they are dating does NOT mean you are ready and peer pressure is not a good reason to start. On the other hand, if they all are and you are the last hold-out, it’s worth examining why. What is the source of your reluctance and hesitation? Do you have some anxieties and concerns that need to be addressed?

2. Do you want to build a home and have a family at this moment in time? And are you prepared to make the sacrifices required? A lot of people (no matter their age!) are too focused on the taking part of marriage and not enough on the giving aspect. Or, to put it another way, they’re not willing to pay the price that a real relationship requires – the subjugation of your own needs, the constant consideration of someone else’s, the new restrictions on time and the new priorities.

3. Have you spent time introspecting and figuring out the answer to these two basic questions: What am I looking for? This should be a short list of essential characteristics and (more importantly) Who do I need to be? Am I working on giving? Selflessness? Kindness? Consideration? Honesty? Loyalty?

I think that an honest (perhaps ruthless) exploration of the above issues will help clarify if you are ready.

If you are – and it’s just fear holding you back – then take a deep breath, offer up a lot of prayers, and jump in!

Good luck.

-- Emuna