Advise! My Boyfriend Has Issues. Should I Stick Around ?

After 4-6 weeks of dating, I’ve been in an exclusive relationship with a man 4 years my junior (I am 36) who has had some significant struggles in his life: he is aware of their impacts and is actively addressing them – most recently leaving a relationship that had activated some of his own issues. As someone who has overcome my own history of dysfunctional family life and personal strife, I admire his commitment to his own health, and empathize with his journey. In many other ways he is also fantastic: he owns several properties, has several degrees in engineering, has managed to find a job where he has ample time for extracurricular activities, maintains a close network of friends, maintains a humble self-perspective, and seems thrilled to be with me: he helps me with things that are difficult (both family strife and car repairs!), enjoys meeting my friends and family; he’s introduced me to his friends and some of his family (with whom he has a very complicated relationship). We seem to share a vision of what our futures look like. He tells me he thinks we complement each other well and that we have a long future ahead of us.

But…his shadow self emerges, and I recognize I am still getting to know him. He has acknowledged that he has an ambivalent-anxious attachment style (with the tendency to retreat when he is feeling emotionally challenged, but still a deep need to connect), which he is making sense of in therapy and independently. But, as someone with an anxious-frightened attachment style, this can be particularly provoking for me. He is always open and available to speak about my needs and feelings – but is not always equipped to handle my expressions. I’ve noticed this can stir up some maybe-not-so-long-lost feelings of abandonment for me, and wonder if this means that we are doomed?!

I can see he genuinely cares about me and is eager to make progress. I wonder about the balance of “wait, grasshopper” and ” believe the negatives” – both of which I have read from your columns. I wonder – should I cut my losses or stick things out a bit longer to find my pot of gold at the end of the rainbow? I know there are other interesting men out there (they are still pursuing me!), but I am still more interested in seeing what this man has to show. Am I deluding myself!


The good:

You have the awareness and self-esteem to realize your boyfriend is not the last man on Earth. At any point in time, if you don’t feel like your relationship is taking, you can always go back to the well and know there is an endless parade of suitors out there.

The bad:

You have anxiety issues. He has avoidance issues. You need more safety and intimacy, and when you don’t get it, you feel triggered. He needs more freedom and space, and when you express your anxieties, he withdraws. Anxious/Avoidant attachment partners are, in my opinion, the worst possible pairing because your needs are, essentially, mirror images of each other.

Anxious/Avoidant attachment partners are, in my opinion, the worst possible pairing because your needs are, essentially, mirror images of each other.

Now what makes things even harder to navigate is this: you’re really stuck on this guy. And you’re writing to me to make sense of what seems like contradictory advice, “wait and see,” or “believe the negatives and run.”

Honestly, you don’t have to decide today.

It sounds to me like he’s a good man, who is into you and is working through his issues.

That’s a huge start. You can’t ask for much more than that, in fact. Which is why I see this situation through a prism of cautious optimism. He’s a man of character. He’s caring.

Why bail on a promising relationship just because there’s a hint of trouble?

Only one reason: fear. And you can’t let fear make your decisions in life. You can’t let fear make your decisions in life.

As I see it, the script of your relationship has yet to be written. Is this man equipped to be your future husband? Only time will tell.

As you’ve identified, there’s a chance he won’t be able to overcome his past, but it seems to me like he has all the best intentions in attempting to do so.

One of my favorite quotes is: “The only risk is the one not taken.”

“The only risk is the one not taken.”

Take the risk, Anne.

It may not work out, but you’ll regret it if you walk away now.

About the Author

A prolific love author who specializes in creating love stories often focused on the romantic connections between people which readers can identify with.