Should I Risk Getting Hurt, Or Settling And Being Unhappy?

I’m a 50-year-old divorced woman with two relatively young children, and I’m dating two men. Both are great guys: accomplished, educated and successful. One of them I have wonderful chemistry with. He’s handsome, articulate and says he is quite smitten with me. We’ve had many special moments together, and he has asked me to be exclusive with him. He’s a recent widower (4 months after a long illness), and is working through the grief, but says that he didn’t expect to meet someone so quickly that “did it for him.” The other gentleman is more emotionally stable (divorced 10 years), and I like him a lot. He’s gentle, kind and has already stated that he is in it for the long haul with. The trouble is, no chemistry. I’ve even been on a road trip with him, and while we talked non-stop the whole 10-hour trip, I couldn’t bring myself to sleep with him. I have not slept with the other gentleman either.

My question is, do I go for the chemistry and the chance that the recent widower will wake up one day and realize that he still misses his late wife and I am simply a salve for his pain, or do I go for the more stable, but less desirable alternative? I figure, either way I’m taking a risk that I will not be happy. But there is also a possibility that either guy could be the ONE. I’m kind of giddy about the widower, and know that if I don’t go for him, he will not last long on the dating scene. He’s also close by, while the other man lives about 40 minutes away, and just texted me 3 times. The widower I see about every other day, and we talk, or IM or text every day. In my mind, most of the good ingredients are there for both men. I’m just afraid of falling in love and getting hurt, or settling and being unhappy. –Kim

Dear Kim,

Your question brings up a very important distinction in the chemistry vs. compatibility debate that has been raging on this blog for years.

You CAN have a chemistry that is a 10 and have a wonderful life together.

And it’s a distinction that I’m afraid gets lost amidst all the shouting, straw man and slippery slope arguments that are used to challenge my assertion that compromise, compatibility and character are the best determining factors in a successful long-term relationship.

You ready? Here goes:

You CAN have a chemistry that is a 10 and have a wonderful life together.

In fact, if you read closely, you’ll see that I’ve never said otherwise.

There’s nothing “wrong” with the 10 chemistry except for the fact that it’s such a powerful force that many women accept an unhealthy relationship – putting up with lack of commitment, emotional abuse, and poor communication just because of that “feeling”.

However, if your 10 chemistry is financially stable, emotionally available, and commitment-oriented, then there is absolutely NO reason that you shouldn’t be with him.


If you put a 10 and a 6, side by side, and, for all intents and purposes, they are equally devoted to you, you should ABSOLUTELY choose the 10.

In my experience, 10’s are risky bets, simply because they know they’re 10’s –which means they can be selfish, narcissistic, unsympathetic, and fickle. Why? Because they CAN be – and women will always put up with them.

But being a 10 in someone’s eyes is not synonymous with being a jerk, nor is it mutually exclusive with being thoughtful and committed.

Being a 10 in someone’s eyes is not synonymous with being a jerk.

Are you taking a risk with a widower? Yes. He’s on the emotional rebound, bigtime. Yet, plenty of widowers simply prefer being married than being alone, and if you’re the first one there, then you may just get lucky.

Just promise me that you won’t stay with this 10 if it turns out that he doesn’t treat you well and he’s ambivalent about your future.

Otherwise, I think you’re in an enviable position.

Tell the 6 that you’re moving on and good luck with your 10!

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  1. 31

    @Natalie, #29
    I agree with you.  And it sounds that even though the decision was somewhat made for her by Mr. Chemistry, it sounds like for different reasons, each one was less than ideal.

    Hopefully the widower (or someone similar who wants what Kim wants and who wants it with her) will come back, but the other man definitely should have been cut loose whether there was another option or not if she was reasonably sure that her feelings for him couldn’t move beyond “just friends.”

    What is funny is how the advice on this blog not to be blinded by chemistry is somehow taken to the level of hyperbole and the idea that chemistry equals bad relationship.  It’s just that lust and extreme chemistry can cause both men and women to make less than rational dating and/or relationship choices.  Interesting that no matter how old you get, the thrill of being with the hot guy or girl never goes away…

    Good luck Kim…hopefully you’ll find the total package out there!!

  2. 32

    Evan, your newsletter today with the tin man/lion analogy struck a chord.   I was told by a friend earlier this year that I need to find myself a “submissive” man! ??   It’s almost as if you are saying something along those lines.  How exactly does one respect such a man? It would be good to see a discussion on this.   

    Apologies for posting this here. 

  3. 33

    Nobody who’s a widower/widow should be dating anyone 4 months after a spouse’s death. I had 3 dates with a widow of almost 2 and half years and she was a robot who kept referring to “her husband” in the present tense.I felt like I was on a date with a married woman. The sad thing is she’s a very attractive women who I could’ve definetly had some chemistry with if she had a personality,could’ve opened up a bit and acted like a normal single woman.After 3 uncomfortable awkward dates that was it.I don’t know that would go near a widow again probably.It’s just not worth the time and money.To be honest,maybe I don’t have the patience it takes for that situation especially when I have other options.

  4. 34

    @Ellen and ValleyForgeLady:

    Kind of bad manners, don’t you think?  While I know Evan encourages people to openly share their opinions, I don’t think personal attacks are warranted.  (Sorry, but I really enjoy this blog and and I don’t want Evan to get fed up and stop doing this!!! 🙂  


    For what it’s worth, I really liked the photo you used in this article!  The woman has a wonderful expression, is beautiful and looks like she is over 30 — an unfortunately rare occurrence in today’s media.

  5. 35

    I can’t say that I’m surprised that either guy didn’t work out.  I went on one date with a gentlemen who’d been widowed for approximately a month and he was ready to sleep with me on the first date.  I had the good sense not to go down that road. 

    With regard to the fellow Kim did not have chemistry with, it’s obvious he was needy and that was a turn off for her. 

  6. 36

    Strong word of advice to Kim  . . . if you decide to ‘get with’ the widower – make HIM wait at least a full year.  In the meantime head over to a site like which has a robust wife of or girlfriend of a widowers board. There are happy relationships with widowers – and then there are these women who have to compete with a ghost.   The biggest red flag in your original message to Evan – 4 months of the dead woman and then he met you.  The red flag in the follow up, “He got scared and will check in every 2 to 4 weeks.”  Honey, he’s not ready.  If he has her clothing, her pictures all over the house, he intends to continue all holidays with HER extended family, etc. etc.  Maybe this is all gone – but I would bet a lot of money . . . it’s not.

    If he comes back – pay attention to those ‘details’ and follow up with Evan. I know he ticks a lot of women off but he’s spot on.  I just think he might have missed the ‘4 months after the long illness of the dead woman’ thing. 

  7. 37

    I would RUN, RUN fast from the widower. Trust me, It happened to me exactly like what you felt – 10 chemistry and his wife died for over 2 yrs when we met but with total of 7 years past, he still decided he wanted to go back with the “dead wife” and to “process his feelings”. Oh My god – please run!!!!!

  8. 38

    Kim 17 and Evan 21 – thank your lucky stars.  I also went out with a widowed man (he had been widowed FIVE YEARS) and my gut feeling said, hm, single, reasonably attractive, but NO NO NO NO NO NO NO.
    I listened to my gut instinct, wondering why the hell my gut was saying that.
    Fast forward – visit to his home – all of his wife’s clothes were in the wardrobe, ditto her photographs and while it’s understandable, it truly gave me the creeps.  By the way, I was the spitting image of his wife!!!!
    He was not over his wife at all.  And I just could not go there.
    He wrote me an absolutely horrible pile of letters when I very kindly said to him, with the utmost tact, that he was not the man for me (no mention of his wife etc.) and those letters was really really abusive.  I kept them for a while, in case his verbal abuse turned nasty or physical.
    I did not reply either.
    No, although I’m single, at least I’m not in that relationship.

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