On Dating the Semi-Decent Man: What’s Your Dealbreaker?

Lately, I’ve been getting a lot of letters from the ladies asking about relationships with semi-decent guys. Y’know, guys who are pretty darn good except for this one niggling detail.

Before I get into the letters, let’s look at an analogy. Let’s say you’re in the market to get a used car (in the relationship marketplace, there are no new cars). Let’s say it’s in excellent shape and you’re getting a fantastic deal, but the back seat has some scratches and stains. Would you still buy the car?

Okay, now let’s say the paint on the passenger door is scratched, and there’s a ding on the rear fender. Or it has a flat tire. Still okay?

Now let’s say the transmission is broken. How about now?

The point is that there is a spectrum of flaws, all the way from utterly forgivable (scratchy paint) to deal-breaking (no transmission). After all, there are certain car-like features that you would like a car to have. And without those, you basically don’t have a car.

Let us now extend this to the realm of relationships. What’s the point of being with a guy anyway? Well, you want to feel safe around him — safer than you would without him. You would want to know that he has the capability to provide for you financially, even if you have your own income. You want to feel loved and nurtured, and have someone who is receptive to your love and nurturance in return. Emotional stability is important. And ideally, his presence would catalyze your growth towards an even better version of you.

I’ve written a whole book on what you should look for in a guy, so I’m not going to get into the details of that here. But I do want to make you aware of what your dealbreakers are. The most basic one is that he hinders your growth as a person.

On the other end of the spectrum resides the “don’t hit on 20” rule, as propounded by my good man Evan Marc Katz. The idea is that in a game of 21 or blackjack, getting cards that add up to 20 is a pretty good result. You don’t want to ask for one more card (or “hit”) when the only card that can help is an ace, and there are only 4 of them in the deck. In other words, nobody’s perfect, so if your guy’s flaws are not dealbreakers, you’d do well to consider keeping him.

Some of these letters are on the long side, so feel free to scroll through them to get to my comments. And if you’re in the mood  to ask me a question, writing me a letter that’s under 200 words makes the likelihood of a response go up exponentially, ahem :)

First one’s nice and short. I’ve pasted my response just as I sent it to her, no fancy caps or nuffin’:

Hello Dr Ali — I have just broken up with my boyfriend because he has a short temper and I think I am really sensitive about this because my father was verbally and physically abusive towards my mother.  When he gets upset or starts swearing I feel myself shutting down and he complains that I don’t communicate with him. I figured that his temper would result in me withdrawing even more if we lived together and started having real problems, at the moment things like a misunderstanding via txt, a bad driver, or a late taxi would really set him off and have me feeling drained. I’ve spoken to him about it and he aid he would never get physical with me and he can’t help his temper and swearing because he is Irish. Apart from that he is a really nice guy, did I do the right thing? We had been dating since September last year, he is 30 and I’m 25.

Thanks Dr Ali :-)

mallory – thanks for the letter! the whole point of a relationship is for two people to practice being loving to one another and grow together in a way that they couldn’t do it on their own. sounds like your fella’s temper here prevents these things from happening. also, you’ve just got to know what your dealbreakers are. if you can’t feel safe enough to express yourself freely around him, esp with your family history, it sounds like a dealbreaker to me.

on the plus side: now you know one of your dealbreakers, and will remember to look out for it in the next relationship :) you’ve made an adult decision towards your greater well-being — congratulations on that. now move forward with an open heart and find new mutually nurturing connections.

best, AB


Next one gets a llittle more complicated:

Dr Ali,

I have a wonderful boyfriend that I’ve been with for about a year. He is a wonderful human being and one of the most genuine kind hearted people ever to walk this planet (no joke, my guy friends tell ME I’m lucky to have found him!)

But I’m 33 and looking for long term stability and although he has everything I want in a man mentally and physically…he’s not financially stable (and we all know this is a huuuuge issue and one of the main causes for divorces, etc). His family culture is very different from mine. His family never pushed him to finish school or let him know of all the opportunities that this world has to offer — my family completely opposite. He didn’t finish his BA (one year left) and he had an hourly job for 8 years (never once asked his boss for a raise).  That was until he met me…I encouraged him and pushed him out of the comfort zone which was so foreign to him. He went back to school and is now in the process of finishing his last year. I asked him to show his boss what he’s done in the past couple of years and ask for a raise and he did that…and got laid off (boss told him he should find another opportunity and he deserved better).  

So now he’s jobless and going to school. While I’m working full time and have recently completed my masters program.  Given our cultural upbringing and financial situation, you can imagine we fight a lot about the same things. I am constantly bitter and frustrated that he does not have a steady source of income yet and that he’s not done w school yet (even tho he is working hard to finish now). 

I’ll be the first to admit, I am extremely ambitious and I want to push him the be the same..but I am forcing the situation. Everyone has their own timeline. Sometimes he tells me I belittle him saying “what 35 year old is still finishing school and have no steady source of income?!” I don’t say this all the time but I do get hard when I am really frustrated. Sometimes I am too blunt with how I feel. But I am also an impatient one and one that likes to go about life my way.

So do you think it’s me? Something I may need to work on…or do you think that him and I are way too different and in the long run…it won’t work out? That’s what I’m trying to figure out now before it is too late but I wonder if it’s just an easy answer. I’ve dated successful people before and they weren’t good partners. He’s an excellent partner and that is why I keep holding on..frustrated and angry and all (which can’t be good).

Please let me know your thoughts… Thank you…Trudy

Trudy –

This is a great letter raising an all-too-common isssue. What do you do with a guy who’s great except for this one niggling detail — which happens to be a dealbreaker?

Because you do have dealbreakers, right? Like being a crack addict. Or physically abusive. Or not being able to provide for his future family.

If you were 25, I would say, hey, he sounds like a great guy, and relationships are all about practicing being loving, so go ahead and have fun with it ’cause you’ve got all kinds of time for now. But if you’re on the market for a husband to start a family with, 35 is kind of go-time. It’s time to make the big decisions.

He sounds like a really sweet fella, but I invite you to do the thought experiment of playing this scenario out over the next ten years. Let’s say you stay with him and get married. He will still be poor and you’ll still be bickering about money. You’ll be bitter because you’re carrying the lioness’s share of the financial burden. He will be bitter because, tacitly and explicitly, you will be questioning his diligence, work ethic, and generativity as a man. You will be ultra-bitter because now his habits don’t affect just you, but also your children (kids were in the plan, right?). He will be ultra-bitter because he feels emasculated and unappreciated even though he’s so so kind. And when you get divorced, you’ll be traumatizing your kids as well as yourself.

On the other hand, if you end it now, there will be a few weeks of moping, and then you’ve both created the space to let in someone who’s a better fit for your lives. As the Tao Te Ching says,

Confront the difficult while it is still easy;

Accomplish the great task by a series of small acts. 

If you take care of this now, without acrimony and from a place of cognizance and compassion, you’ll both be much better off in the long run. But if you postpone this decision until you reach a breaking point and a decision forces itself, then you’ll be much worse off.

Also, you mention several time cultural differences. What are they exactly? Context matters. And finally — what is your question here, Judy? What do you want? Think that through and get back to me.

best, AB

You raise a great point, Dr…and we are on the same page with thinking of 10 years down the line, etc.  but there is a difference if he’s in fact working towards being better (versus sitting around and not trying to change anything, right)? He’s acknowledged my needs and has asked me to be patient and that he will do all these things to make our lives better. I’ve already seen subtle changes and he’s fully back in school with a few more months to go. So given that he’s actually taken some action, would your advice still stand? I’ve communicated to him that this is a deal breaker and he fully understands and wants to change. He’s Warned me that it is 35 years of habit that he’s trying to change but he sees the value and wants to move forward and change for the betterment of himself.  

In any case, I have just been impatient with his pace of change….but I’ve only been with him for 11 months. Who knows? In 12 months he would be out of school and may have a great job. He’s not lazy at all…just didn’t have a reason to be motivated in the past (or just simply lost in life). But these days, he wakes up at the crack of dawn, studies and works on his portfolio…he’s definitely changed. I’m just wondering if I wait for someone like this or move on to the next (and potentially find someone successful that I don’t end up clicking with….or finding no one at all). Is the grass greener on the other side type of thinking. 

The cultural difference (our upbringing): my family culture is to work hard, have financial freedom, earn a prestigious degree, get a great job in a respectable profession etc..and suffer in the short term to gain some stability in the long term, even if you’re not happy (traditional Asian families…go figure). His family culture is spending time with loved ones, we are ok as long as everyone is healthy, being there for each other, less about money and prestige but do what makes you happy, etc.  On one end, it’s all about the fundamentals (money, job, stability) – my family never expressed or showed their love, we should just know because our parents paid for our college tuition.  On the other end, it’s expression of love, family, togetherness, compassion, understanding etc..the softer side. Two extremes..which makes our thinking so different. But he’s open to looking at things from my perspective and I am the same with him.  We’ve both improved ourselves from learning from each other but a long way to go.

I must admit…his family and personality has caused a balance in my life. I was always constantly stressed and my parents and I love each other but we fight a lot and do not show affection (no hugs, no I love yous…it’s just awkward)….and when I’m around his family…constant hugs, great conversations and openness. I think this is why I love him. He balances me on a personal level and that is another deal breaker that he DOES have and its battling with the monetary deal breaker (in which he’s currently trying to fix the situation).

What I want is to be able to trust and be more patient…11 months is a while but it’s not like he is sitting on his ass. He’s doing something. But my parents have always rushed me and pushed me to the point where I would break down…and I think I am doing the same to him. I’m telling him his pace is not fast enough for me…but I do want to be with him because he is doing his best. So my question is…how can I practice being patient? I am on a faster track but it should be ok because I believe he will get there too. How can I not ruin this for myself (there’s no doubt in my mind that in a year, he will be successfully up and running)? 

Thank you…

Trudy –

Thanks for the clarification (a bit shorter next time, please :)

If you make enough money and that’s not an issue, and this man really opens your heart and provides warmth and love in ways you’ve never experienced before, that’s one story. If he’s a grown man who can’t support himself or you and this is a problem, that’s a whole different story altogether.

If you just want to hang out with this guy and have fun, then there’s not a lot of harm in it. But if you’re 33 and your eventual goal is marriage, my recommendation is to avoid fixer-uppers. You are not a guy trainer. And you are not his mother. You are a fully-grown woman looking for an equal in a relationship to catalyze greater love and growth for both of you. And chances are there is a warm, open-hearted guy out there right now who’s already got his act together and would make a great partner for you.

Now I don’t know the facts, never met the fella, and don’t know what you’re like together. But I do know that when a woman is making a lot of excuses for her partner, it’s because she’s with the wrong guy. A great partner who’s a good fit requires no explanation to anybody.

So think about these things. It’s possible that you also need to work on your ambition overdrive, impatience, and emotional coldness. However, that’s your job and your responsibility. In the same way, his progress to diligence and financial solvency is his job. Once again, it’s not your place to be his partner AND his mother. It sounds like part of your super-diligent Asian upbringing is your belief in the ability to fix things and succeed with hard work. And I’m telling you, Trudy, that it’s not your job to fix this guy. No project boyfriends, please! Go for pre-fabricated.

So figure out if all this is a deal breaker. If not, stick around. If it is, break the deal and move on without regrets.

best, AB


This next letter is epic. The players are already married, and there’s a fair amount of backstory that I won’t fault you for skipping. Feel free to scroll down to my response if you don’t want to read the whole thing (remember: 200 words or less!):

Dear Dr Ali — I’m in a difficult situation and would really appreciate your thoughts on my relationship. I know this email will be longer but my situation is unique and I want to include as many relevant details as possible. I’m a 24-year-old woman married to a man in his late 30s. We met online and spent around 2 years in a long distance relationship because we were in different countries. I know you’re not a fan of LDRs but despite the tough times it worked for us. We constantly kept in contact and were very loyal to each other. Eventually he moved here to the U.S. to be with me and we got married.

Things were great for about a year but then a lot of issues cropped up. My husband fell into depression because he felt like he didn’t deserve me (long story, but he had a troubled past and felt things were just too good to be true) and it resulted in him not “coming to the party.” While I worked he sulked at home or half-heartedly made attempts to find a job. During this time I focused on being supportive of him because I know depression is a nasty beast, but it definitely took its toll on me. I started resenting the fact that his depression was stronger than the drive he felt to be actively engaged in our relationship and contribute monetarily to the household.

The issue relating to money really bugged me because my mother was very supportive of our relationship despite initial misgivings, and even helped send him to college to get a certificate in one of his hobbies as a gift. Yet there he was doing nothing with it and just sort of slogging along.

After a full year of depression he came out of it and things got better for a while. He worked several different jobs but due to chronic pain from an old injury (another contributor to his mental state) he wasn’t able to sustain them for long. At last he found a place of work where he didn’t have to move around a lot throughout the day, played to his strengths and started bringing in good money. I felt like we were finally getting back on track.

The problem? To start, I had lost most of my sexual interest in him. I was really excited to experiment the first year he was here, and in fact my husband was the first and only man I’ve ever been with. I am a fit, attractive and “go-getter” sort of woman if I do say so myself, but I was never really interested in guys my age because they were all so immature. It was a great experience being with my husband at first even though he is overweight because we had such a great mental connection and our personalities meshed. But after his “time off” I ended up losing confidence/trust in him, and honestly, some respect as well. My sex drive plummeted and he still wanted to be active, but I feel there is a block preventing me from wanting to be with him intimately again.

He has now just gone through a leave of absence at his job due to his chronic pain. I don’t doubt he will return to it more dedicated than ever – it is very debilitating for him at times but he really wants to recover as much as possible and do more with me. It’s just hard. He goes with me to events as much as he can, but thinking of our future, I imagine travel, sporty hobbies, etc, and I know he will not be able to do all these things with me.

It hasn’t been a “long” time but just in these past 4 years I realize I didn’t honestly consider how his mental health and chronic pain would have such a strong effect on my life. Initially I was too caught up in how much I loved him and how wonderfully we meshed. It hurts me so much to think of leaving him, and I wonder if I’m not strong enough to hold up my end of the marriage. You do say “in sickness and in health,” and here I am thinking of abandoning him. 

He has never been cruel to me, and despite all our hard times, he is amazing at communicating openly with me and learning from his missteps. He loves me more than anything and even when I’ve told him about these things I’m feeling, he says he understands and doesn’t blame me. He’s willing to let me go because he doesn’t want me to put my life on hold for him or simply stay because I feel bad, but at the same time of course he doesn’t want me to leave.

I don’t know what to do. He is an incredible person, so kind and intelligent, funny, always has good advice for me. Despite the age difference we have tons of similar interests and I’ve always felt comfortable with him. Our relationship has survived despite so many odds and I think of what the trade-off would be… leave him for what? A younger guy that might give me more physical satisfaction but never take my words to heart like he does? I know there are billions of people out there and surely, somewhere, there is a guy my age who is also thoughtful and would share my interests – with the bonus of being more physically capable – but why throw away the loving relationship I have now for the chance of that?

There’s something to be said for every person in the world being unique and no one else is exactly like my husband. I love everything about him except for how this horrible and frustrating pain sabotages his life, and I know he feels the same. He used to be very fit, sporty and athletic and it’s like the injury has taken away a fundamental part of who he is. He’s my best friend and I love him, I just don’t know if it’s wise for us to be in a romantic relationship together. I have even considered an open marriage – staying with him while “playing” with other guys, which he is understandably a bit iffy about, but hasn’t completely rejected the idea.

I don’t want to lose him, and I want to be there for him… yet when I see cute guys giving me looks it’s so tempting to start flirting with them and I’ve never felt that draw before. I guess at this stage I’ve started wondering if I missed out on anything, or if I’ll miss out in the future. I feel like a terrible person and wish there was some way I could just regain my passion for our sex life.

What I want in life is to be able to explore my passions, run a successful business, help people and travel. In the midst of that I’d like to keep growing as a person, and I think the right partner can help you do that. I’d like to be with someone understanding, but also someone who pushes me to do and be “more.” 

As for what I want in a partner: pretty much all the things my husband is (funny, kind, intelligent, honest, supportive), but I’d be lying if I said I didn’t also want an exciting sex life and someone who could keep up with me in the physical department. I’m not sure if it’s me not working hard enough to renew our sex life, or if knowing his pain will prevent him from doing the aforementioned things making me check out. 

My question: Am I missing out on a better partner for me, maybe even a better life? Or would I be tossing away a perfectly good relationship because I haven’t come to terms with the pain my husband faces, which is beyond his control? (He has tried all different kinds of therapy and surgery over the years but nothing has fixed it.)  

Best regards, Carin

Awright, Carin. Just seeing the facts in someone else’s writing is sometimes enough to snap one back to one’s senses, so allow me to summarize:

  • You were 18 when you met him, he was 32. You met on an online video game site.
  • You spent two years with him in a long-distance relationship before marrying him. Since a long-distance relationship is no relationship at all, you really didn’t know him that well, or what it would be like for you to be together, as your letter amply demonstrates.
  • He is severely out of shape, depressed, and financially unstable.
  • You have lost your sexual attraction to him.
  • His bad moods and disabilities bring you down. A lot.

Now I’d like you to imagine your 50 yr old self who has an 18 yr old daughter, about to embark on these very same decisions? What would you say to her?

Probably something along the line of this: “Are you flippin’ crazy?!?”

In other words, these were a series of very, very bad decisions. Marrying someone you met online? At the age of 20? Who’s 14 years older than you?

Of course, you were 18 yrs old. Bad decisions are a teenager’s hobby.

The good news is that now you’re in a position to rectify those errors, instead of doubling down on them. I’ve said it before and I’ll say it again, until everyone remembers it:

As far as anyone can tell, we have one purpose in the world, and that is to be of service. Therefore, you have no right to be with someone who sucks up all your energy, diminishes your light, and keeps you from your full flourishing. That means it would be unbelievably selfish of you to STAY with him. You owe it to yourself and the rest of the world to move on. 

This doesn’t mean you have to stop loving him. Please keep loving him! It’s a beautiful and precious thing, and you guys can be friends forever if you play your cards right. But it does not have to be in the context of romantic partnership. Sometimes it’s much easier to love someone from a distance.

Above all, you’re only 24. And nowadays, no 24 yr old has any business being married. Go have fun! Figure out who you are, what your preferences are, feed your ambition, date a bunch of hot dudes who can take you dancing and kitesurfing and mountain climbing. I don’t believe anyone would fault you for ending the marriage at this point. Moreover, your parents will probably sigh a giant sigh of relief when you do so.

So, to answer your question: yes, you are missing out on someone who’s potentially a much better fit as a partner. It’s very sweet that you care for him and feel obligated to stick around. And I know you promised “In sickness and in health” in front of a lot of friends and family, but I’m here to tell you that you were not qualified to make that promise at age 20, and any promise containing the word “forever” is a silly promise anyway. But there are fundamental mismatches between you two on so many levels, and you two are not a good fit. All that is holding you back — and will continue to hold you back unless you move on. Time to let go and start the rest of your life afresh.

Whew, that was a long one. Now here’s the thing: how do you remember these principles when it matters most, before you make the big decisions? This is like asking how to make sure you’re ready to run when you need to catch a bus (or run away from a bad guy). The answer is you want to be fit, all the time. And fitness is a continuous, daily habit, not a one-time thing. And the purpose of all my writings, books and courses it get you fit such that you can capture opportunity when it arises and handle peril when it shows up.

To that end, you can read books like The Tao of Dating and do its exercises, and that’s always a great start. Or for deeper training of the principles, you can enroll in Project Irresistible and spend 6-8 weeks with the Tao of Dating principles instead of 6-8 hours. The course cannot be skimmed like a book, and it can’t gather dust on a shelf. So you will have no choice but to learn about things like: your personal values and how to align them with your love life; finding your true self; mindfulness and meditation; being your own best mentor; expanding your comfort zone; embodying your physical presence; and creating more of your own best opportunities for love. Like most things in life, you get out of it what you put into it since it’s a self-directed course. But it’s a much more potent learning experience than just words on a page.

I’ve also started doing one-on-one consults again focusing on behavioral change. I’m happy to help if there’s a good fit between my expertise and your needs, and I’ve kept my prices well within the realm of reason. Send an email to DrAli(at)TaoOfDating.com if you’d like to explore that.

Eager to hear your stories and questions, so do send them along (under 200 words! have a question! mention age and location!). In the meantime, remember that the quality of your life is directly proportional to the quality of your decisions, so if you do get good advice, be sure to implement it. And chime in with your experiences and what you think the ladies should do in the comments below.

Best, Dr Ali

1 Comment on “On Dating the Semi-Decent Man: What’s Your Dealbreaker?”

  1. Deb Bell

    I read mostly through the first two. Your responses were great, from what I read. Trudy should keep her guy. Having an affectionate family around is priceless. He’s amping it up a bit, she needs to practice bringing it down a bit. Great balance. Kids need both.