Firstly, it is wonderful to see that you have acknowledged past mistakes and are seeking God's will for your life. Let's start by addressing all how you can overcome your negative self image and how that you are trying to make corrections in your own strength. Moreover, let's address the financial distress weighing you down, and the issues with your relationship, Owen, and your families.
1 John 1:9 says If we confess our sins, he is faithful and righteous to forgive us the sins, and to cleanse us from all unrighteousness. It is great to see this in action, however turn the past to God completely and do not attempt to change in your strength but by His grace.
When attempting to change, then 2 Corinthians 12:9 explains that Each time he said, My grace is sufficient for you, for my power is made perfect in weakness. So then I would rather boast in my weaknesses, that the power of Messiah may rest on me. It is a matter of trusting that nothing in life can come to you without passing through God first and believing that all He allows is out of love for you. Then the weaknesses do not bother you as much.
Next, praying for reconciliation with Owen is commendable, but keep in mind to pray this with a desire for God's will. Recognize that if Owen is not a Christian believer, this is a prayer that demands repentence first before it can be honored.
2 Corinthians 6:14 says Do not be unequally yoked with unbelievers, for what fellowship have righteousness and iniquity? Or what communion has light with darkness? This is about relationships, business, ministering, and possibly marriage between one believer and one unbeliever. His unsaved position will hinder your relationship with God and pull you away from your destiny.
Proverbs 19:14 says House and riches are an inheritance from fathers, But a prudent wife is from Yahweh. Moreover 2 Corinthians 6:14 says Do not be unequally yoked with unbelievers.
Seeing Owen as a future spouse creates a situation that merits caution, if he is not a believer.
Our Lord Jesus Christ wants us to focus on our relationship with Him and live according to His Word. Pattern your prayers to reflect this fact and ask that if it is His will.
Pray for you and Owen to grow individually in your relationships with Christ. If you both seek God's will, He will bring you together. It very simple when trusting God.
About sexual relations and co-habitating. Seeing the infactuation that you having then co-habitation is a possibility to surrender to sexual sins.
Romans 13:9 says For this, You shall not commit adultery, You shall not murder, You shall not steal, You shall not give false testimony, You shall not covet, and if there is any other commandment, it is summed up in this word, Love your neighbor as yourself. Everything about life is about our relationship with others. Our love and guidance to others reflects God's love.
Hebrews 13:4 states that marriage is honorable in all, and the bed undefiled, but God will judge the sexually immoral and adulterers. Do not be indifferent to scripture passages like this one.
Concerning the financial worries, take courage. Review Matthew 6:25-34 and trust God for his provision with way to have money to place in the bank (banking advised).
First, pray for a job, no matter how small, and let your faith be in action. A prayer request for financial blessings or a specific amount of money will likely be answered with a responsibility to perform as a source.
Moreover, defend Owen, by praying that given he has a rebellious heart, then that he may have experiences with God (Hebrews 3:7), no arrogance (1 Peter 5:5) and growing in God's Word (2 Timothy 3:16). Then, 1 Timothy 6:3-16 mentions false teachers will love money and teach unholy behavior. Meekness and contentment lead to prosperity.
When facing pressures, request the Fruits of the Spirit (Galatians 5:22) to assist to resist bad interpersonal relationships and withstand any pressures caused by them. God will assist family members to improve their love for one another (John 14:15).