Dear Guilty,

Trust is a two way street. Yes, your boyfriend should try to trust you, but in return you should also do your best to reassure him and behave in a trustworthy fashion.

You Need To Earn His Trust

C'mon Vivi, everyone has a past.

You mentioned that your boyfriend is concerned that "with your history" you should not be trusted to hang out with your numerous male friends. If there is something in your history, some indiscretion you participated in that makes your boyfriend jealous or worried, then it is up to you to do the work necessary to earn his trust again. Even if that means cutting back on time spent with the boys.

I get the sense from your letter that you hold your friends in very high regard. This is wonderful, but if your boyfriend feels like he's always playing second fiddle to your crew of male friends, it could be a source of tension and jealousy.

You commented that you would dump your boyfriend if he interfered with your relationship with your best (male) friend. Yes, you are correct to feel protective of that relationship with your best friend, but if you have presented this threat to your boyfriend ("don't mess with us or I'll dump you") then perhaps that gave him even more reason to feel threatened by the whole concept of you spending time with your male friends.

Consider Your Partner First

That's not the point. She should be able to hang out with whomever she wants.

I think in the healthiest long term relationships, your partner becomes numero uno in your life, or at least as important as any friend in your life. Even when we've got hectic work and social lives, a couple needs to work to keep their partner reassured that they are still important.

He Shouldn't Be Reading Your Email

Finally you mention your email in-box. Why is your boyfriend snooping in there in the first place? Even if you are trying to hide something (not to suggest you are), your in-box is private, and your boyfriend should keep out.

Like I said, your boyfriend should try to trust you, a good place to start would be to take his nose out of your email. But you should also try to meet him half way, let him know he is the number one priority, that your friends will never come between the two of you. If there really is some "history" that gives him reason to worry, then think about cutting back some on the time you spend with the guys.

It's unlikely that the problem here lies squarely on his or your shoulders, so you both have a little work to do. Good Luck!

–