Apparently three times really may be the charm in this case.  Britney Spears may be walking down the isle with her boyfriend and manager, Jason Trawick.  Rumor has it that when Spears wraps up her Femme Fatale tour, Trawick will finally pop the big question after years of dating.  According to RadarOnline, Spears is under a conservetorship, which simply means her father is in charge of her financial assets and well being.  If Spears decides to get married, her father’s lawyer will have to sign off on the union.  Spear’s family and two sons, Sean Preston and Jayden James, love Trawick and can’t wait for him to join the family.

How do you know when to pop the question?

Cupid’s Advice:

Proposing can be nerve racking, no matter how long you’ve been dating your partner.  Fear of rejection and long time commitment can put an engagement on hold.  Here are some ways to know you’re ready:

1. Family: If your family is crazy about your partner, then he or she is likely a keeper. Do either of you have children?  If you have already begun to raise kids as a team, it might be time to make it official.

2. You find yourself looking at rings: Talking about marriage and kids is one thing, but actually window shopping or surfing the net for a ring may mean that your ready to take the next step in your relationship.

3. Commitment: An engagement means a commitment to each other, and the ring lets other men and women know that your partner is happily taken.  Some couples decide to stay engaged and forget marriage, while others enjoy a long engagement before sealing the deal.  Whatever you and your partner choose, if you’re in love and ready to make a commitment, its time to pop the question.

When did you know it was time to ask, “will you marry me?” Share your experiences below.