I think a lot of people have a hard time asking for forgiveness because doing so requires genuine humility, and showing humility leaves one open and vulnerable. We are so intent on guarding our hearts that it becomes too hard to express the sorrow and shame that accompany humility. Part of this is that we do not set a supportive stage for the "forgiveness exchange" to occur, and fear of rejection and further shame prevent us from making ourselves vulnerable. And of course, we know that perfect love casts out fear, which means we are not operating in love when we do not reach out and ask forgiveness. This is why the love of the Lord Jesus - the love that motivated him to the cross - must be our motivating factor in giving and asking for forgiveness. Love for God first, because we desire to obey him by reconciling our relationships, and love for our neighbour that we have offended second.
When we are reluctant to ask someone to forgive us, we need to search our heart to see the fear that is operating, and then pray that Jesus' love would replace that fear and humility would replace our pride.
