“When you are stuck in conflict with your partner, before negotiating with them, first listen in order to get to know them better. Your partner needs to do the same for you.”

Mixed Signals: How Do I Know What He Really Means?

Note: This letter was edited for clarity.

Dear Dr. Deb,

I’m 57 years old, happy, and confident with myself and my life. But I’m in the middle of a murky situation that leaves me feeling like a confused teenager. 

I’ve been seeing this guy casually. Or at least, I think I am.

We started off as friends. At the time, we were both trapped in horrible relationships. We confided in each other, and this made us closer.

After our respective relationships ended, we started hooking up. He shows signs of interest in me, and it seemed like he wanted to get more serious with our relationship. But just when I thought we were going somewhere, he pulled away. I didn’t stop him and gave him space.

Lately, we started talking again. It’s been going well, seemingly getting back on track. But then he started sending me videos of people ending their relationships and joking about having commitment issues. It felt like a passive aggressive way to pull away from me again.

Dr. Deb, how do I know for sure what he means by this? What do I do about his hot-cold actions?

At A Loss

Incapable of Loyalty?

Note: The narrative and question in the letter have been edited for clarity

Dear Dr. Deb,

I have been reading your new column and really appreciate all the honest advice you’ve given. I’ve considered writing to you several times before, but my relationship problems have always seemed to resolve themselves.

This time, it’s different.

Let me begin by saying that I think the world of my girlfriend. She’s intelligent, adventurous, and we laugh a lot. Not to mention that she’s beautiful. We’re both in our thirties and have been dating for about eight months. I really care about her. It’s a big plus that we both grew up in Catholic families and share similar values. Despite dating a relatively short time, I occasionally daydream about our future together.

The bad news is that she’s been diagnosed with bipolar 2 disorder. She began having symptoms when she was 19 years old. She experienced cycles of depression and manic hypersexual behavior, which is one of the characteristics of the disorder. But at the time, she felt too embarrassed to tell her psychiatrist about her hypersexual behavior. She ended up getting misdiagnosed and improperly medicated. It wasn’t until years later that she told her doctor about it and finally got help and the right treatment for her sexual dysfunction. 

Since we began dating, she’s seemed emotionally stable. But deep down, I’ve always felt that we should be talking about her mental illness and discuss how it could affect our relationship. I know it’s easier said than done, and it seems like we’re able to talk openly about all this only when we’ve both been drinking. 

In these “sessions,” I’ve told her that I’m a fiercely loyal, monogamous person. I’ve admitted to infidelity as a dealbreaker for me, and I’m worried that her disorder will jeopardize our relationship. She has tried to reassure me by saying that her episodes of acting out sexually and recklessly are simply part of her bipolar struggle and not a relationship related issue. I don’t feel reassured at all.

Dr. Deb, I do love her, and I don’t want to break off our relationship, but should I commit to someone who can’t offer me the stability and monogamy in return because of her condition?   

Is it time to cut my losses and end this or is there a way to work this out?

Fiercely Loyal

Left with Less on the Weekends

Note: the question was edited for context and clarity

Dear Dr. Deb,

My husband is currently struggling with executive functioning and emotional dysregulation disorder related to ADHD. He’s been working with his doctor to get his medications just right, and finally, after several combinations, it looks like he’s found one that works really well.

By well, I mean that when he is on his meds, he is a conscientious, loving, patient man. But when he misses taking them, he is short-tempered, has no filter, and can’t concentrate. The trouble is, he says the meds make him feel “not like himself,” so he only wants to take them during the week when he needs to work. On the weekends, he often skips them or “forgets” to take them until it’s too late (he gets insomnia if he doesn’t take them early in the day). My kids and I are then left dealing with his issues.

I feel like it’s unfair that we never get his best self on the days we spend with him. But he feels like his family should understand that he doesn’t want to be medicated 24/7. When I try to explain that it’s hard on us deal with him when he’s scatter-brained and temperamental, he gets defensive and says I only “love him when he’s on drugs.” 

What should I do?

Deprived and Disappointed

Stuck in an Emotional Rollercoaster

Note: This has been edited for clarity.

Dear Dr. Deb,

My partner cannot meet my emotional needs. That aside, I think we have a wonderful relationship. He’s  everything I want. But the emotional part is huge – and he admits he isn’t capable of handling that. 

He avoids emotions and takes anything that touches on that as an attack, which leaves me walking on  eggshells and feeling like I can’t be myself around him. 

He started counselling because he says he realizes he needs to work on himself, but honestly his behavior  has gotten worse since then. It’s a cycle of highs, and lows, and I’m having a hard time ending it. I don’t  know what to do.  

I feel lost. 


Separated and Holding on for an Answer

Note: Letter edited for clarity

Dear Dr. Deb,

I’ve been reading your columns and I admire how reasonable and non-judgmental your advice seems to be.

My husband and I are currently separated, and I am concerned that this might lead to divorce.

This is my second marriage, and we have two children. Hubby has a history of alcoholism, although he’s been sober over nine months now. 

When our first child was born in February 2016, my husband decided to quit his job of 17 years to stay home with the baby and me while I healed. We were married a few months later, in June 2016.

I returned to work that September, but not my husband. He hasn’t worked a real job – meaning any work situation longer than three months – since the birth of our first child. Our second child was born in May 2019. Then the pandemic hit.

We started living in separate homes in September 2020. I bought a house in December 2021, but he refuses to live with me and my mom. I completely understand that. We are still both in New York, but each living separately with our mothers. The children live with me and visit him every other weekend.

I have no interest in being in another intimate relationship with someone else, but I dislike catering to him as a wife and not getting 100% of the benefits of having a husband. No Social Security is building up in his account. I pay for every date night or family trip. I don’t even have the pleasure or luxury of waking up to hubby’s face in the morning.

My question is: how much longer should I wait for him to get a job? Is our separation leading to divorce?

Separated and Holding On

When Business Gets Personal

Dear Dr. Deb,

My thirteen-year marriage is falling apart.  It’s hard to tell who’s really at fault, but I do want to untangle this mess and understand the role I played in it.

I’m a 55-year-old recovering drug addict who’s remained sober for 20 years. My wife is an only child who grew up with alcoholic parents.

Several years ago, I left my corporate tech job to become an equal partner in my wife’s very successful real estate business. We both wanted to create a true partnership built on our mutual desire for fulfilling work while making time to live the life we love. Our company roles focused on the different skillsets we brought to the table: I took on the COO role, and she continued to lead as the CEO.

However, the honeymoon was short-lived. Business issues soon surfaced concerning decision-making and conflicting work styles.  Being a type A perfectionist, my wife refers to the business as “her child going off to college.” In my case, I don’t feel like a “birth-father” to the company, and I have trouble referring to the business as “ours” as her identity is so closely entwined with it.

For example, she rejects my opinions frequently, insisting that she’s more equipped to know what’s best since she was responsible for the initial success of the business. I’m constantly afraid of letting her down, which means I tend to defer to her decisions often. Ironically, this seems to frustrate her even more.

She fluctuates between being supportive and being demanding, pressuring me to know more than I do. I get emotionally overwhelmed, so I detach and don’t communicate — as a former techie, I’m used to isolating myself.

Sadly, it seems we’ve become adversaries. Neither of us feels nurtured by the other. Our sex life is non-existent. Home is no longer our sanctuary because we can’t seem to separate our personal relationship and the business.

I feel powerless and hopeless, and I’m being mindful of the potential effects of this conflict on my sobriety. Thankfully, I’m still able to keep myself drug-free. Dr. Deb, can you help me figure out what I need to do with my two roles as a husband and business partner to deal with this situation? 

Keeping Sober

Twice Betrayed and Having Second Thoughts

Dear Dr. Deb

I’m the kind of person who doesn’t make decisions lightly. Once I’ve made up my mind, I can’t be convinced otherwise. So when I decided to enlist in the Air Force to serve my country in Afghanistan, neither my mother nor my wife could change my mind.

Several years ago, sometime after my discharge, I discovered that my wife was having an affair with her colleague. She ended it, and after much coaxing on her part, I put my ego aside and agreed to give our marriage another shot. It sounds cliché, but I made that decision partly because I was worried how the divorce would affect our three young children.

My one condition was that if she had another affair, divorce would be non-negotiable.

To my great disappointment, I recently found new emails from her lover that showed that she hasn’t learned her lesson. This time, I’ve decided to move out of the house.

Of course, neither me nor my wife are perfect. We certainly had our fair share of issues before her infidelities. It seems that I’d become too self-absorbed, insensitive, and prone to rages. I’ve often been isolating in my home office which has become my sanctuary away from her and my family.

But here’s where things get even more complicated. During our separation, my wife and I have continued having sex and seem to be enjoy each other’s company again. We’re even managing to co-parent peacefully.

WTF is happening?

In my heart of hearts, I believe that I need to be firm about my choice to leave the marriage. My mother supports this decision, and I know where she’s coming from: I’ve witnessed her agony and eventual recovery over my father’s philandering and their inevitable divorce.

If I stay in my marriage, I’m not sure I’d get over the feelings of resentment and shame. On the other hand, my wife and I seem to be in a good place. So I’m wondering now: Am I being too rash and ego-driven about wanting a divorce?

Twice Betrayed

Just (Online) “Friends”?

Dear Dr. Deb

I am a 55 year-old married man, happily devoted to my wonderful wife of 30 years.  She is smart, beautiful, kind, and funny.  We have recently become empty nesters, and I’m loving the independence.

Several months ago, while noodling through the internet, I met a woman who, like me, is an avid motorcycle rider. We have become internet chat friends, talking about everything from motorcycles, to politics, and more.  There is nothing sexual about our conversations.

The problem, Dr. Deb, that my wife feels disconnected from me and deeply betrayed.  Convinced I am cheating, she has taken to annoyingly hover over me when I am at my computer, which is slowly alienating me from her.

I love her and would never cheat on her. However, we have become distanced and have reached an impasse in our relationship.  


Deeply Befuddled

Dear Dr. Deb

I need your help.  I can’t find a man who loves me for me and I don’t know why.

I’m 55, divorced, and, although this may sound vain, still quite attractive. I have a very healthy self-esteem and with good reason. I built a successful real estate career, made a ton of money, and I drive a Bentley!  Yet with all I’ve got, I haven’t been happy.

I was in a lonely marriage to a cold and remote man. I knew I deserved more, which is why I divorced him. But rather than finding a loving companion, I ended up with a series of Lotharios. It starts out with romance and affection, which ends up with me funding their “dream businesses, which never go anywhere. Of course, when I realize this and stop being a cash cow, these jerks get nasty and manipulative.  Rather than being loved, I feel used. These losers have cost me several MILLION dollars!

Dr. Deb, how did I become such a victim?  I’ve heard a lot of these things are rooted in childhood experiences, but I couldn’t have had a happier one. My adoptive parents loved me, showered me with attention and reminded me I was everything they ever wanted in a daughter. Sure, they had strong ideas about the kind of person I should become, which wasn’t necessarily what I wanted for myself, but they’ve guided me well and I trusted they knew best.  

This makes it even harder for me to figure out.  Dr. Deb, how could I be so smart in business and so stupid in men?

Deeply Befuddled

I Used to be Her Rock, but Now I’m Drowning

Dear Dr. Deb.

Last week I had a sinking sense that I was lost.  Lost in myself and my life, that is. Nothing seems to make sense anymore.  The thing is, I can’t shake this feeling that the only way to find myself is to get out of my marriage.  NOW.

Am I having a mid-life crisis? I’m a 43-year-old biracial man married to a white woman.  We’ve been together for 12 years, and we used to be happy.

I always thought we were a good match.  I’m a tech entrepreneur and she’s an MBA student, always on the Dean’s list and still manages to juggle a part time job as an accountant.  Early on I did recognize that she can be emotionally needy.  She would have crying jags and bouts of anxiety that would affect both our routines and our social life.  I couldn’t go to my parents’ 40th anniversary party because she was anxious about the people there.  It can be exhausting and I feel like I am dealing with a troubled child.

To be honest, I think I’m partly to blame for her behavior.  I liked being someone she looked to for strength and guidance.  I’m very empathetic and have always found it hard to turn down people who need my help, even when I sometimes feel like I’m running on empty.

But, now I feel trapped.  Helping her with her emotions has taken over my life.  I love her, but I feel like I’m at the end of my rope.  All I want to do is get as far away as I can from her and her meltdowns because I feel like I’m drowning.  Dr. Deb, is leaving my wife the only way to regain a sense of myself?


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