You’ve chosen to dismiss that tired adage “once a player, always a player” and give that charming guy a chance. However, dating someone with a bad reputation can intensify normal stumbling blocks, perhaps leading you to wonder if the relationship is worth the doubts you feel. When you get to the bottom of his player rep, and learn how to trust him as well as your own judgment, you may find that insecurities and anxiety fade.

His Bad Reputation

Perhaps the stories typifying your beau as a past player are exaggerated. Your best bet for getting to the bottom of his reputation is to have an honest talk with him. On the other hand, maybe your guy confirms his past dubious behavior but vows he has changed or will. Even when he’s on his best behavior, you’ll have to contend with the fact that his reputation is “sticky” and will probably only be dispelled in his social circles when he has shown commitment to his new dating philosophy for quite some time, as represented by findings of a study by University of Missouri anthropologist Shane J. Macfarlan and fellow researchers, published in "The Royal Society" in 2013. If you’re going to have a successful relationship with him, you’ll need to be willing to rely on your own judgment and tune out the voices that continue making jabs about his past ways.

Understanding Jealousy

When you believe your dating partner has given you probable cause to keep your ears perked for suspect behavior, it can be hard to distinguish normal jealousy from the type of intuitive worry that could indicate something is wrong. Jealousy can crop up as you grow closer to someone simply because you stand more to lose, asserts the Healthy Place article, “Jealousy Can Destroy a Relationship.” To not be swept away by jealous impulses, objectively look at his behavior and remind yourself that feeling somewhat possessive can be a normal part of adjusting to the relationship and does not necessarily mean there’s a problem.

When the Going Gets Tough

The capacity for being part of a healthy, mutually trusting couple is determined in large part by reactions to small moments, explains researcher John Gottman in his Greater Good video, “How to Build Trust.” When one individual not only refrains from helping the other in a time of need but also thinks, “I can find someone better” or “I shouldn’t have to deal with this,” the trust begins to rapidly deteriorate. If his past playing around was a matter of not wanting to be weighed down by a romantic partner’s problems, proceed with caution. Tell him how you think two people in a relationship should handle obstacles and find out if his views are compatible.

Helping Yourself

Best case scenario is that your boyfriend is forthright, demonstrates he has grown up and builds trust through a series of loyal acts. If this doesn’t transpire – if, instead, his eye keeps wandering and you keep feeling let down – it might be time to look at why you were drawn to him in the first place. Some girls fall for guys who display such noxious characteristics as narcissism because such guys are able to effectively “sell themselves,” suggests clinical psychologist Vinita Mehta in the "Psychology Today" piece, “Why Do Women Fall for Bad Boys?” Ask yourself if sporadically being the recipient of his charm is worth the negative emotions you’re probably feeling, from anxiety to self-doubt. If you know in your head that the relationship is bad for your emotional health but you just can’t seem to let it go, consider enlisting a therapist or peer counselor, or at least a trusted loved one, to help you sort out your thoughts about him, dating and your self-worth.