Should I Choose My Old Flame Over My Safe Boyfriend?

Should I Choose My Old Flame Over My Safe Boyfriend?

Evan, I’ve been involved with Ken for two years. I met him through friends. He isn’t exactly who I envisioned and we’ve had some tough challenges along the way. I think he’s handsome, and I know he’s ethical, devoted and loves me totally. I love him too but my physical attraction to him has never been strong.

I took a break from him when my Mom died and went back to my hometown. I was praying to my Mom and God to help me to know the way. And then standing at the foot of the lake I met Jim from my High School. It was instant attraction for both of us. We have much in common and there is a sense of joy I’ve not known before. Here’s the catch. Jim had a long affair while he was married which he told me without prompting.

I got scared and Ken kept working to win me back. What I have with Ken is very good. He’s a great friend, I like him and we have things in common too. But I still think of Jim and I know he thinks of me.

I don’t want to throw something away with Ken and have regret. Jim feels we’re meant for each other and his family and friends do too. How do I come to what’s best for everyone?

I would love your insight very much. It’s been thrilling to see your success.

Warm Regards,

Dear Patty,

My heart breaks for you, darling.

You lost your Mom and your head is reeling.

You’re praying to God for dating advice.

You’re thinking of giving up your ethical devoted boyfriend for a man who is a proven cheater.

And if that wasn’t enough, you’re asking to “come to what’s best for everyone.”

The only person who decides what’s best for you is YOU. Got it?

Really, you’re making this way harder on yourself than you have to.

Let’s work backwards.

His family and friends think it’s best if you’re with High School Cheater Jim. Fuck them. They don’t have a vote.

Neither does High School Cheater Jim or Devoted Ken. They want what’s best for them, not what’s best for you.

The only person who decides what’s best for you is YOU. Got it?

Everyone else’s opinions are irrelevant. Yes, including my own.

But that’s not gonna stop me, of course.

Now, let’s understand that there are exceptions to every rule and aphorism out there. But that doesn’t mean that there isn’t truth to be found in: “When someone shows you who he is, believe him.” And “One in the hand is worth two in the bush.”

Jim has shown you who he is. He’s an admitted cheater and borderline homewrecker who is trying to leverage the weight of his family and friends to convince you to leave your relationship.

You want to willfully ignore all this because you feel more attraction towards him.


You HAVE a man who is husband-worthy. How do I know this when I’ve never even met him? It’s because you’ve chosen to date him for two years — and most women aren’t big on wasting time on men who don’t have husband potential. You’ve described him as “handsome, ethical, devoted and loves me totally.” And you wrote: “What I have with Ken is very good. He’s a great friend, I like him and we have things in common too.”

And you’re willing to throw that all away for the wild-card that is Jim.

I know: the heart wants what the heart wants.

But does the heart really know what it’s doing? And is it actually the heart that’s making your decisions for you? I’m betting it’s not.

Barry Schwartz, author of “The Paradox of Choice”, spoke to Lori Gottlieb when she was writing “Marry Him” .

He put things in a very plainspoken way that I’d like to paraphrase for you, Patty.

I know: the heart wants what the heart wants. But does the heart really know what it’s doing? And is it actually the heart that’s making your decisions for you?

Basically, he said, we have to make choices with tradeoffs. When you find an amazing guy, like Ken, who may be an 8 on a 1-10 scale, you think of him as marriage material. But then, after a few years, you get accustomed to him. You see his flaws. He becomes more predictable and less exciting. Suddenly, your feelings drop from an 8 to a 6.

You start telling yourself that you could do better. And along comes a guy like Jim. Your attraction to him makes him feel like a 10.

You make your decision. You’re going to toss out your 8 (who turned into a 6) for an exciting, passionate 10.


What you haven’t calculated is this:

Your “10” is going to have his own set of issues, which you may or may not be able to deal with on a daily basis. Attraction is not a solid foundation for a long-term relationship. Good communication and shared values is a much better predictor of success.

So you may be thrilled to get that extra rush of dopamine that comes from your initial attraction to Ken, but one day, that feeling is going to subside — for both of you.

Alas, your 10 will magically morph into a 6 as well. You may be able to put up with his issues (anger, jealousy, bossy, stubborn, busy?) but Jim may decide that, after a few years of marriage to you, that he’d like to find a 10 that he’s more passionate about.

That’s right. Even if your feelings for Jim stay strong, there will always be an undercurrent of fear in your relationship.

It would be like being in the witness protection program; all you can do is hope that the status quo continues to hold. You pray that the cheater has really retired from cheating, even though you have no control over his actions.

So, to bring it on home, when thinking of building a 40-year relationship, you’d better ask who is the safer bet.

Is it the ethical, devoted guy? Or the cheater?

I don’t judge you for choosing the cheater.

But I wouldn’t be surprised if I got another email from you in 5 years either.

Join our conversation (63 Comments).
Click Here To Leave Your Comment Below.


  1. 1

    This is very similar to something I went through.   I was having a relationship with my “high school” boyfriend – also an admitted cheater.   He ended up going back to his ex-girl friend after we dated for almost a years when she decided she wanted him back (after he cheated on her).   He also admittedly cheated on his wife for many years.   A year later I meet my husband.   He is sweet, giving, we have the same values and interests.   He treats me like a princess.   We date for 2 1/2 years and then get engaged.   When  ex high school boyfriend finds out  he decides he doesn’t want to be with ex girlfriend anymore and wants me back.   Ex high school boyfriend and I always had very good chemistry and for a split second I wondered if I was making a mistake with current husband – but that was as long as it lasted – a split second.   I realized very quickly that my boyfriend (now my husband) was the one I should stick with.   It was definitely the right choice.   I knew that what I had with ex-boyfriend was all chemical based.   He had a way of making anyone  feel really good.   But you know, I soon realized it may not last long and he had a history of cheating so I made the best decision I could for me.   It was the right decision.  

    1. 1.1

      I’m going through the same thing right now, we broke up 2 weeks ago (not officially, though, I packed my bags when I saw a text from his ex, asked him what it was about, and as I expected he told me that it was nothing; not that it would have mattered what excuse he would have came up with anyway but I told him to take me home and he hasn’t said a word since then, except for when he brought me my glasses and when we met at college and acted like nothing happened). I know he wasn’t good for me but it hurts so much thinking that I was just a rebound and he didn’t give a damn about me. We’ve had so many beautiful moments together and he just tossed it all away.

      Since then I’ve started online dating and out of all the guys so far one of them asked me on a date and he always calls and wants to talk all the time (unlike my ex), told him about what happened in my past relationship and is very understanding. There is not really chemistry with this guy and I miss the thrill and the buterflies (I still had buterflies after 9 months), but I keep telling myself that buterflies don’t respect you, call you, commit to you etc.

      This new guy is even more attractive (physically) than the ex, but the ex was the first guy I slept with and in the beginning he was very patient too and adored me (I was a 20 yo virgin and so far most of the guys I had dated broke up because of that, until I met him: a cheater who respected who I was and waited until I was ready). Everyone could  acknowledge our chemistry, and I guess that’s what kept me going, until it didn’t anymore. I still want that but I know now that it’s better to choose stability and commitment over anything else.

  2. 2

    solid advice. Its normal to seek greener pastures when we are faced with potentially spending the rest of our lives with someone, hopefully sense will prevail over lust.

  3. 3

    Evan, you hit the ball out of the park with this post. Excellent post. I would have given the exact same advice. I honestly believe that to follow attraction in this case will lead the disaster. You bring up a really valid point when you mention this guy is leveraging his family and friends to get the woman to leave her relationship. In all honesty, I don’t think I could be with a guy if he wanted me to leave a perfectly healthy relationship for the sake of attraction, which is also going to eventually fade just as it has with Guy A. And like Evan said, who is to say this Guy B won’t find a woman he’s more attracted to, especially since he has a history of cheating and is also trying to break up this woman’s relationship. If somebody puts such a high empahsis on attraction they are always going to be disappointed. You will always find someone else you’re more attracted to. But the grass isn’t always greener on the other side of the fence. I have watched plenty of folks I have known throughout the years who followed attraction and its whims, and not only did they end up hurting a lot of people, but ended up hurting themselves too.

    And let’s face it, even  if you find the most perfect partner for you there will come a point in your relationship with him that you won’t feel that same attraction that you did in the beginning. It’s not just a matter of “if”, it’s “when.” It’s part of being in a long term relationship. I’m sure this “husband material” guy can name things that he doesn’t find so attractive about this woman too. Relationships are hard work. And if someone really wants that awesome relationship they need to be willing to keep up the hard work, even when they don’t feel like it. Otherwise you will always be jumping ship for  someone else and wondering why you’re alone.    

    1. 3.1

      Yes! Thanks for the thoughtful reply

  4. 4

    I’m not convinced that playing it safe is a good strategy here. Nor is hyper risk taking. The way I see it, from how she writes about her boyfriend and the circumstances around the high school flame, neither are excellent options. We don’t know the nature of the problems that have happened historically with the boyfriend, but the OP’s comments about him are strained. She’s trying to show his good points, but the way she talks about him doesn’t sound like a woman who’s interested enough in him for the long haul. Chasing the old flame is simply flipping to the opposite side of the coin. She’s tossing worries about having to muster enough interest for a man who may not have the skills to maintain anything long term. It’s a common pattern. Leaving stable, but ultimately lacking relationships for what end up being extended flings filled with passion, followed by messy break ups when reality returns.
    At the end of the day, Patty needs to decide if she really can envision a life with the boyfriend, or if she’s just keeping him around because he sounds good on paper. To me, that relationship is the lynchpin. Decide now to truly stick it out, or to leave on good terms. The other guy can wait.

    1. 4.1

      In this case, I actually liked your response better than Evan’s. While I completely agree that the high schools crush is absolutely not an option due to his rather obvious flaws, I also think Evan kind of missed the fact that it seems the current boyfriend is obviously not an option for her either.

      She mentions that she’s never been that physically attracted to him (which  hasn’t improved over the years),  and the way she made it sound, it’s likely less than the 6-7 Evan generally recommends.  The way she made it sound also makes me wonder about her contentment with their physical relationship in general.

      And she does seem to actually have to try to find reasons to  be interested or excited about him at all. Obviously, there’s a lot lacking in this relationship, and she isn’t too happy right now either.

      Which makes me wonder if that is the reason the old high school sweetheart holds so much appeal to begin with.

      I think she should stay away from the high school crush, but also possibly reevaluate her current relationship. Seems a bit like she’s settling too much in order to avoid being alone.

      And that if she stays with her current boyfriend, the temptation to cheat, or be with someone else will continue to cause problems over the years.

    2. 4.2

      Very interesting. Although Patty framed her question as a choice between A and Z, it really isn’t, or shouldn’t be.

      The real question is whether she is truly devoted to A and should stay with him, or should leave and seek something that can be a life-long love.

      The high school flame is simply not a good bet, as Evan explained so well.    Guys like that are often seeking excitement, and hoo boy they can generate excitement – but they tend to leave when relationships settle into some comfortableness after a couple years.

  5. 5

    Evan, I think there are a lot of women willing to “waste time” on someone for two years, depending on their age.   If the OP is 27, sure.   Especially with the attraction thing.   (I wouldn’t assume that because someone is divorced, they necessarily had a long marriage or are older.   My cousin was a 27-year-old divorce, I graduated high school with a girl who has been divorced twice and has a baby with a third guy, and we are 30).

    OP, Evan is right.   You are the only one who should make this call.  

    You know, at the end of the day, this attraction to Jim may just really be an wake-up call that you should be evaluating your role in both relationships.   Maybe you should sort of meditate on “What is Jim’s purpose in my life? What is he here to show me?” as opposed to “Who do I pick?”   Also, Jim’s determination that you are “meant to be” is a bit dramatic.  

    I don’t think “Once a cheater, always a cheater,” but I do think everything is circumstantial and the fact that he had a LONG, ongoing affair while married is the bigger tip-off.   Post-divorcees as well as people in grief, such as your self, are emotionally wide open.   You may very well be the passionate rebound that Jim was seeking.

    Either way, a co-worker of mine is taking a human sexuality class and told me about the different “Love Styles”.  

    I think this is relevant to this letter, and also to many people who read this blog, because we may very well be “Eros” (passionate/romantic) but it feels like we are being forced to be “Pragma” (driven by the head/marriage as a business transaction).   I honestly think that attraction is necessary and if there is NO physical chemistry at all, you are always going to be longing for that.   Maybe I’m over-reading into this, but a lifetime of bad sex isn’t something I’d want to sign up for. But a lifetime of deep passion isn’t totally necessary either.   I kind of think the best option is (c) an individual who you are attracted to, that is also kind and devoted.   If you AREN’T attracted to Ken, not one bit, it is a chore to have sex with him instead of something you look forward to, you aren’t doing yourself any favors by lying to yourself.

  6. 6

    Great advice, but somehow agree with Nathan’s comment. Just seems like none of the guys would be IT. That’s just how it seems from afar.  
    Good luck to the OP. Hope she finds the right way for her.

  7. 7

    PS One more thing I’ve learned regarding regret:

    Patience is also a virtue.   Because you walked away, and a few days later, a new option popped in, that doesn’t make it THE other option.   It makes it AN other option.   Rarely is the next thing we encounter, the best option.   (“Rebound” is a well-known thing for a reason).

    You really haven’t, at the core, decided upon what it is you need in a relationship.   If you did, you could communicate it to Ken or would have left him after a couple months knowing it is “going nowhere”.   I’ve met wonderful Ken types who I felt zero attraction to.   We lasted a month or so, because I didn’t enjoy kissing them.   If you ever had physical chemistry with Ken, maybe you can find that, but it isn’t looking that way.

  8. 8

    I’m not sure she should be with either guy. Though you can’t maintain the initial feeling about a guy at the same level years in, you should still feel excited about your guy and feel lucky to have him if he’s a marriage prospect.  

  9. 9

    I agree with Nathan– she doesn’t sound thrilled enough about Ken, and meeting Jim just highlights what’s missing for her in the relationship.   Patty, first forget about Jim and evaluate your relationship with Ken.   Stay with him or leave him independent of Jim.   You don’t have to stay with him just because he loves you and has objectively good qualities– stay with him if you love him and can see a future with him (don’t end up like the OP from a few weeks ago who ignored the issues and ended up in a bad marriage!).   Then, if you leave, you can think about Jim, who at this point seems like hardly more than a fantasy.   

    1. 9.1

      Great answer.

      I feel bad not because my current boyfriend lives paycheck-to-paycheck, has no car, waits tables for a living and rents a room.

      I feel bad because all that bothers me. The ex is a doctor who treated me like a queen (until he left to go back to his second ex-wife).

      Btw, we are 60, not in our 20s.

  10. 10

    I agree- the fact that the old flame is distracting her from her 2 year relationship doesn’t mean the high school guy is right for her, but it does mean that Ken may NOT be right for her. If she’s so easily distracted, how much in love with Ken can she really be? 2 years is not THAT long to have been with someone for passion to fade – a lot of couples are still super-loved-up at that point. The only important decision here is whether she wants to be with Ken or not – Jim is an irrelevance. She needs to take a decision about Ken WITHOUT assuming Jim is going to be there if she leaves. he may be – he may not be. Each of these things is a separate decision.

  11. 11

    The fact that Patty says “my physical attraction to him has never been strong”. is a huge red flag. Attraction is not the only thing between people but it is important and is the basis/foundation for many other things that follow in any relationship, like mental and emotional attraction. I don’t think high school cheater Jim is the right option but her current boyfriend might not be either. Five years into a marriage with him and she could be the one having an affair. Think about it Evan, and other readers out there, what if your significant other admitted to you that their physical attraction to you had never been strong. OUCH! That would be a pretty big blow.

    1. 11.1
      Evan Marc Katz

      All the folks who see this as a sign to dump the devoted boyfriend, Ken, please read this latest New York Times article, which reiterates everything that I’ve ever said here.

      Eventually, all love turns into companionship. It takes a smart and strong couple to keep things interesting when you have, by nature, a stable and predictable life together. The problems are that: most couples are not smart and strong. They don’t understand that it’s virtually impossible to be EXCITED by someone after 2 years. It’s appreciation. It’s comfort. It’s friendship. It’s laughter. And yes, it can be great sex, too, but, as always, that’s an activity that a couple needs to communicate about. Someone can become better in bed if it means pleasing his wife sexually and rejuvenating a marriage. It’s a much more achievable goal than turning a cheater into a loyal man.

      So when I hear the OP say only this, “I think he’s handsome, and I know he’s ethical, devoted and loves me totally. I love him too but my physical attraction to him has never been strong,” and your first conclusion is that she should DUMP this man? You’re only indicating that you think that it would be a better bet for her to try to find another handsome, ethical, loving, devoted boyfriend who has just a little more OOMPH. Sorry, my friends, but that’s bad advice.

      And if you don’t believe your happily married dating coach, perhaps you can believe all the scientists who have informed my opinion: marriage isn’t a passionfest. You don’t get excited about your “new” car after five years and you’re not gonna get excited by your spouse in five years, but that doesn’t mean you can’t have an amazing marriage with a good sex life if you work at communicating and keeping things lively.

      1. 11.1.1

        To say that these people’s opinions are wrong for having lived through their own experiences is not very responsible from a person in a position of giving advise. Just because you yourself are in a positive relationship doesn’t make it exact.

        In my experience, choosing the ‘safe’ route doesn’t always work. After 15 years choosing the ‘safe’ partner over the ‘passionate’ partner led to disaster. Who’s to say what circumstances arise? Every relationship is different. They bend, form, change and it is dependant on SO many things that to make a blank statement that anyone who thinks this woman should leave the ‘safe’ choice is BAD advice, is irresponsible.

        It doesn’t matter how long a relationship it is. Everyone moves at a different pace. Instead maybe look at what’s causing the confusion. There is no doubt a root cause. None of us want to make the wrong or a bad choice when choosing the person we want to spend our lives with. I think it might just be a decision on what we are willing to compromise to make a relationship flourish. It definitely sounds like she has doubts about both of these men. If she has doubts at this stage, that’s something to address don’t you think?

        You’re absolutely right that she needs to make a decision on what’s best for HER and not anyone else, but then you criticise those who may suggest that she chooses neither of these men and infer that she should stay with her boyfriend. That’s contradicting and not very helpful on helping her determine why she is having these doubts to begin with. If you read through her statements, maybe she is indicating that although Ken has all of these amazing qualities, she is just not into him as much as she ‘should’ be and that is why she is confused. Don’t know, just a thought??

        This is just my OPINION and she really should find out why she is having doubts. Even though Ken might be an amazing man, he might just not be quite a perfect fit for her. Two years is probably right timing to start realising certain aspects of a relationship and make decisions based on that.

        Again, just my opinion.

      2. 11.1.2


        And your initial response was totally brilliant – I practically stood up and cheered!

      3. 11.1.3

        Personally, how attracted I was to someone from the onset plays a significant role down the line, years later. True, it’s impossible to get excited about a lover years later as familiarity breeds in but the difference is I would still want to have sex with them or I wouldn’t mind them having sex with me. On the other hand, if attraction was low from the beginning, our relationship will become sexless. So yes after several years all relationships become companionships and the excitement settles      due to familiarity but ones level of attraction off the bat I think determines whether the relationship becomes one filled with routine familiar sex or the relationship becomes sexless. There’s research on how sex dwindles with each year based on how often couples were doing it from the beginning. It’s fair to say couples who are really into each other sexually i.e high chemistry will be having the most sex initially. So in effect, unless people with low attraction levels are having lots of sex, it basically means a lot of compatibility marriages will become sexless few years later.   I am saying that for me personally, if I marry someone based on compatibility with low attraction, it will become a sexless relationship after sometime.

        1. Evan Marc Katz

          I look forward to you sharing me the part where I said you should be in a relationship with “low attraction.” 15 years doing this; never said such a thing.

  12. 12

    Maybe neither guy is it But that brings up another good question. What is she really seeking in a relationship? I ask this because the OP said with the high school boyfriend she felt joy for the first time. I think some good soul searching might be in order because if you’re looking for another person to be your source of happiness you will always end up disappointed with others. Maybe neither guy is right for her. But are the guys the true issue, or is something else going on within the OP that she needs to sort for herself before trying to get into another relationship? If you can’t feel joy and excitment on your own then you’ll constantly searching for it with someone else, and the search will never end.

  13. 13

    Sounds to me like her being with Ken was basically a bit of “I’ll bide my time with him until someone better comes along”, from the get-go, if she wasn’t really that attracted to him from the start.

  14. 14

    I love it when Evan  drops the “f” bomb!  

  15. 15

    Patty, you sound like you are ‘chasing a feeling’ with the old school sweetheard Jim. Cheaters will be cheaters and liars will be liars. Jim has already admitted to cheating and one can almost guarantee it won’t be the last with guys who do this sort of thing. You know leopards don’t change their spots and it’s a big red flag waving there so step back and have a really good think about what is really happening here.
    He’s already told he who he is – a cheater – so listen up.  
    You won’t be the exception to his rule once ‘that feeling’ has worn off and life gets real, the kids are screaming, bills have to be paid and you’re cleaning the toilet yet again. Thats what real life is Patty but if you have a good guy who sticks by you, loves you  and supports you without bailing out into some other womans bed when  real life hits you’ve got a good man.


  16. 16

    @ Evan 15

    I do agree with your point.   But there is also a difference between basic attraction and passion/lust etc.   It’s not about a “little more OOMPH”, it’s about actually wanting any sort of intimate interaction with that person (and maybe the OP is young or inexperienced, and hasn’t developed that physical side of herself fully, and meeting Jim made her realize this).

    At the end of the day, if you aren’t attracted to someone but they are loyal, devoted, caring and objectively good-looking, they are your friend and that’s all. I don’t know how the OP is supposed to find attraction if it never existed.   Lack of attraction isn’t some random “flaw” like “He listens to bad music”… Lack of attraction is like telling a gay man to marry a woman (in the most extreme of circumstances).   Sure, he can be happy and meet all his goals for a marriage, but over the course of a lifetime, if you don’t want to have sex with someone it is entirely different from the passion has died out, etc.

    But only the OP knows which is the true case.

  17. 17

    I agree with evan at 15.
    Intense physical attraction is a trick of nature, memory, pheromones, DNA. It tells you nothing about whether the person is good prospect for a relationship. It doesn’t even mean the sex will be that great because when you stop marvelling over the attraction you might even realise that the sex is just… okay, if that.
    by all means admire the view and feel the butterflies but sometimes you just gotta step away from the light.
    i do find my boyfriend physically attractive but it,s mellow and comfortable, not fireworks. he finds me attractive but it doesnt seem to be the most important thing to him. We just get on and enjoy each other,s company.
    I guess I have the dubious advantage of having experienced the fireworks and   saw it all turn to garbage. I know it means nothing.   
    For the OP, i know the new guy isn,t right and I,m not sure about the current one either. It sounds too rocky.     

  18. 18
    Some other Steve

    I think Evan is being generous to Jim by suggesting that he’ll drop only to a 6.

  19. 19

    This is such an excellent post! I love you when Evan is real and cusses! 🙂

    Also, what I have noticed is when a woman moves on and finds a new man, especially a FIANCE, the ex comes running back EVEN WHEN HE REALLY DOESNT EVEN WANT HER. He is being competitive.

    I say you WILL regret it if you leave.   

  20. 20

    Frankly speaking, if OP trying to choose between two men – she doesn’t love either of them. And none of them is “right” for her, alas.
    If she would love, the question simply wouldn’t appear in her head at all.

Leave a Reply

Your email address will not be published. Required fields are marked *