My girlfriend and I have been dating on and off for over two years. In the beginning, one thing keeping our relationship stagnant was the fact that I thought I had romantic feelings toward one of my closest female friends of five years, and had admitted this to my girlfriend. When I realized I did not have these feelings for the friend, I was ecstatic and fully committed to my girlfriend. The last eight months have been some of the greatest of my life—that is, except when this friend and I try to make plans to see one another. My girlfriend becomes abrasive and questions everything about the interaction, claiming it's a "date." She calls and texts constantly, and I have even caught her reading texts to my friend behind my back. There are few men in my line of work and I interact with other women on a daily basis, and this type of erratic behavior is uncommon of the character my girlfriend maintains from day to day. This has begun to frustrate me to the point that I dread ever bringing up the subject of seeing this friend. The friend and I have seen each other very few times in the last two years as a direct result. Though I understand that my girlfriend has reason to feel uncomfortable about it, I do not understand how she can trust me unquestioningly in any other situation except this one. Is my girlfriend's attitude something she may overcome on her own with time or is it a red flag for our relationship that she cannot get along with one of my best friends (who has no idea of what has happened and tries to be nice to my girlfriend)? —Stuck in the Middle

He Said: Your girlfriend has a good chance of getting over her jealousy if you do some work. Right now, it doesn’t seem unreasonable for your on-and-off girlfriend of two years to be suspicious of your five-year friendship with a woman you may have been in love with as recently as eight months ago. At this point, her suspicions are both a realistic response and a challenge.
 
You can’t control your girlfriend’s mistrust, but you can take steps to dispel it. She needs consistent actions over time that not only demonstrate your affection but more importantly your preference for her over your friend. If your girlfriend is at all perceptive, she is totally aware that you currently think she is erratic, untrusting, and that you dread talking with her about your friend. You said the last eight months have been some of the best in your life; probably for your girlfriend too. Focus on what more she needs from you to feel your love and trust. Maybe, for example, tell her she can read the texts from your friend, or ask her what time, place and frequency would be OK for you to meet your friend. Then give your girlfriend veto rights to change her mind. Here’s a great way to show her she is your number one: you didn’t say your friend had a boyfriend, so I’m assuming she doesn’t. Since your relationship with your friend is totally platonic why not offer to set her up with one of your single guy friends?  That would be OK with you right? Cause if not, you have even more work to do.

She Said:
I've read your question to no fewer than half a dozen women—all smart, self-sufficient, professional, rational women—and not one jaw remained off the floor. I say this so that you can take in what I'm about to say next and know it is not some personal reaction of my own, but a general reaction that any woman would have to this situation and your poor handling of it.

Dude, you are clueless. Most girlfriends are perfectly fine with their men having longtime platonic female friends. But admitting you are in love with a friend, and that it is the one thing holding you back from commitment, and then expecting your girlfriend to act just fine simply because you had a "realization" that you weren't in love, is completely, utterly unreasonable. But what scares me most is that you use your girlfriend's very reasonable insecurity in this one particular instance (when you see that she's secure and trusting in all others) to actually question her character. Instead, you need to look in the mirror, ask yourself what you want, and if it's your girlfriend, then stop this nonsense, and only see your friend in groups or on double dates, when your girlfriend is present.

Your self-description says it all: You are not yet committed to your girlfriend, but stuck. There is indeed a huge red flag here, and that red flag is you.