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If you're engaged to a man who constantly checks out other women, run! If he does this before you get married, you can be sure he'll continue to do that after marriage.
It's normal for couples to have issues that come up when they get married. Finances is often one of them. Talk about it! Consider holding a weekly conference together in which each of you brings up one item for discussion. That will present the opportunity to bring up issues that concern you the most.
It's important to focus on the present and future state of your marriage, but it's just as important to look back to the past. You must deal with past failures before you can put them behind you.
Is it possible to put the past behind you and start over? Time will not solve the hurts of your past failures. Healing comes when you're willing to confess your failures and change your behavior.
You can't make room for the new until you get rid of the old.