She Wants to Date Mr. Low Self-Esteem

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I need some advice about a man I find terribly confusing. I have been interested in this guy going on 4 years – when we first met I was with someone but the chemistry between us was pretty obvious – it was even to the guy I was with. This man is clearly attracted to me and likes being around me, he has invited me out, and gone out with me on several occasions, and even invited me to spend time with him at his home alone. As we’ve gotten to know each other I’ve found some perplexing differences between what he says and what he does that bother me, so I need some perspective.

Each time we went out he would talk about dating and ask me about my relationships, which was fine because we were technically friends. For the past two years, he has told me about the inner workings of his dating life and it seems quite dire. He sees about 2-3 women a month

low self esteem

through online dating sites. The way he describes these women – which I believe is sincere – make them sound like obviously less than desirable prospects to a normal guy. Interestingly enough ALL of these women dump him after 2-3 dates … every-single-time. He says women just disappear on him or stop responding – two women he liked dumped him on the same day. He’s an average guy … not terribly attractive … kind of awkward actually … women aren’t beating his door down.

He’s 42, stable, extremely gregarious, and says he wants a long-term relationship with a family and the whole sha-bang. Unfortunately, he has never been in a committed long term relationship: no kids, no pets, no plants. He says he cannot find anyone who is cool enough … but I don’t believe it. Several women from our job (who are not like the girls he usually dates) asked him out for a friendly date and he turned them down. Yet, he did date a 23 year old young woman from our job and it didn’t work out. During one of our outings he revealed that he was not bold enough to be with a woman that is good for him because he thinks he isn’t good enough.(?)

Needless to say I’ve been on the case for a while. I’m ten years younger than him, very pretty, sexy, smart, spunky, with a good sense of humor and am everything this guy claims he wants in a lady. So about a month ago I made thoughtful efforts to strengthen our friendship with the hopes of it developing in to a romantic friendship. Slightly troubled by his bizarre dating habits I asked different men I trusted what they thought about the serial dating but passing over more logical dating choices. They all screamed “RED FLAG!” and told me to run for the hills. They claim that there are clearly glitches in his ability to connect with others. They insist he has problems, but finally I bit the bullet and asked him out – and he turned me down!

Here are my questions: did he do me a favor (I know he respects me and likes me)? What’s with the serial dating at 42? Is he just a player? Why do sleazy women continually discard him? Regardless of whether he was actually interested in me or not, why would a guy whose clock is seriously ticking continually choose throwback chicks that dump him and actively refuse to go out with a woman who can actually give him what he wants (or says he wants)?

I just would like to make more sense of his behavior. Any insight would be greatly appreciated.


Thanks for writing in. Let me distill down everything you said into just a few sentences, and I think it will start to make some sense. First of all, he typically dates easy women who are socially beneath him – yet these women dump him after two or three dates. Second, he said he seldom dates women from work because he says he doesn’t think he is good enough. Plus – he’s never been in a committed long’term relationship ‘ and he’s age forty-two.

It sounds to me like he has a significant self-confidence issue – he has no self-confidence when it comes to women and dating. This would explain why he dates the “easy women” who are beneath him socially. The fact that he cannot KEEP those easy women around means that even if he scores with one temporarily, his lack of self-confidence makes him a total turn-off in their eyes (and so they dump him). The “no confidence” dead giveaway is his comment about not being good enough to date women at work … clearly blanket statements like that indicate low self esteem on his part.

Now to address your specific questions. You asked if he did you a favor by him turning you down for a date, and my answer is yes – he probably did do you a favor by turning you down … because if you went out with him a few times, you’d get exposed to his true self-confidence issues, and that might not pretty. [He might have a small unit … or he may just be timid sexually … or <insert something uncomfortable here> … you get the idea.] Your relationship would end, and your friendship would suffer … so at least this way, you still have the friendship, right? Your next question was, “what’s with the serial dating at age 42 … is he just a player?” My answer is that he might appear to be a player, but he’s an unintentional one, at best. I do give him credit for continuing to TRY TO DATE, but it seems to me that he needs to address his underlying issues before he will find success in terms of any relationship. The sleazy/easy women dump him because he’s able to hide his true colors for the first date or two … but then whatever issues he has come right to the surface, and cause them to dump him. And your last / most important question about why wouldn’t he date a woman (like you) who can give him everything he says he wants and needs? The answer is – he’s too scared he’ll let you down … which is exactly his self-confidence/self-esteem issue.

Now if it was him writing me (instead of you), I’d suggest he get some counseling to address the reasons behind his lack of self-esteem and self-confidence. He may have had things occur during his childhood that he has not been able to deal with that are causing some of this. Once he knows the root cause of his issues, and is put on a path to deal with them – then I’d suggest he thoroughly read the Midlife Dating Advice section here on – as that will guide him through the midlife dating landscape, give him ideas on how to tune up his personality and his appearance, and also help him to create a measurable dating strategy that will get him what he wants – a beautiful, smart woman (like you) to spend his life with (or least the next three months … ha ha).

Was that helpful, ma’am?

You should consider joining our Midlife Discussion Forum here on There we discuss many issues – including some similar to this. Give it a look, and consider it, okay?

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About the Author

Midlife Bachelor chronicles lifestyle, dating, and relationship experiences and advice to avoid a midlife crisis. Readers like you are often beyond young adulthood in their 30’s, 40’s, and 50’s that want to understand how dating, sex, relationships, and love fit in with our lifestyles.