Question: I’m 16 and have been in a relationship for 1 year and 7 months. My boyfriend loves me a lot but constantly hurts me with his silly jokes and comments. He quickly gets defensive and angry about petty issues and just says whatever comes to his mind, but his words hurt so bad. We broke up 3 months ago, but I took him back because he apologized. Now I’m afraid it’s going to happen again and it’s hard to forgive some of the things he said in the past. What should I do? Continue to date him and wait for it to happen again, or break up and enjoy the freedom of being alone?

Answer: It is tough to date a guy with no filter–especially when you are the butt of his jokes and angry comments. You gave him a second chance, and while I’d like to say that should have been all it took to get him to cut it out, I know that it isn’t easy for him to change his behavior.

If he really loves you and you keep reminding him that this really hurts you, he should be motivated to stop by the fear of losing you for good.

Take an honest assessment of how often this happens and how negatively it impacts you. If he makes a comment or two every now and then, maybe you can let it slide. But if this happens more often than not and is making you upset, do not give him a third chance.

Break up with him-not because you don’t enjoy being with him when he’s not making these comments, but because you are better than waiting around for a guy to stop being careless with your heart.

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About the Expert: Rachel RUSSO, MS, MFT is one of Your Monthly Mentors, a Matchmaker, Dating & Relationship Coach, Author & Speaker. She has a master’s degree in Marriage & Family Therapy from Iona College, a BA in Psychology from Rutgers University, and a certification as an Intentional Relationship Coach. Rachel is the founder of Rachel Russo Relationships-a NYC-based dating and relationship consultancy-and has worked as a matchmaker for twelve years. She currently acts as the resident relationship expert on Brooklyn Savvy Tv, is a matchmaker with Lisa Clampitt Matchmaking, and trains entrepreneurs at Matchmaking Institute. Her drive, credentials, and unique experience make her the ultimate dating and relationship expert. Read More…