Navigating the Complexities of Dating a Friend's Widow: Ask Amy's Advice

A man is contemplating rekindling a relationship with the widow of his late friend, whom he had been close friends with before she married his friend. After years of regret, he wants to approach her to see if she has any interest in pursuing a romantic relationship. Despite feeling conflicted due to their past connections, he believes life is too short to not try to make himself happy. Amy Dickinson encourages him to pursue the relationship, emphasizing that love is long and wishing him the best.