Can he really drop his little black book for a family?

by mssinglemama on March 24, 2008



Read his response here. Unfortunately he didn’t answer our question. But, hey, can you blame him? It’s a tough one.

Dear Random Esquire,

We’re kind of embarrassed to admit this, but we’re glad you discovered us. We’re also glad that we’ve sparked what seems like a minor fascination, on your part, in single moms. It’s flattering, but it also has us both questioning your motives.

Rather than send this via e-mail, we wanted to shed light on the obvious nuances we’ve all been leaving in comments on each other’s blogs. We don’t like keeping our readers in the dark, especially when there’s a chance for them to learn a few of our own lessons as single dating moms.

So who are you?

We do know a few things. You are an amazing writer. You make us laugh every day. You’re extremely charming. Oh and you’re also a successful lawyer in Chicago who has an ugly little dog whom you’ve aptly named, “Little Filthy.” And even that is adorable. The only thing you’re missing is a cape.So what’s the catch? We think we’ve found one and we want you to either a) come clean b) tell us what your true motives are or c) come to terms with the fact that you’re just not ready for single moms and to cease all flirtatious e-mails to us immediately.

Single Mom Seeking and I have been blogging friends for a while. And when I discovered your blog…so did she. It started with a few harmless comments and ended with e-mails to both of us on the side.

And then we compared notes and discovered that you were telling us the same things:

1. You think single moms are hot
2. You have a soft spot for mothers
3. You like strong, passionate women

And lastly, (this is the real doozie):

4. You’d rather have a family than a little black book.

You delivered the same lines to two different single moms. And, you had us both for a minute there. But we’re not alone. Look at the fluttering of females who respond to every one of your posts. Are you e-mailing all of them too?

Despite all of this, we still like you. And even though you won’t tell us your name — or post your photo – we don’t want to write you off just yet. Why? Because you represent the quintessential bachelor. And, guys like you drive us nuts with frustration and excitement.

Here’s the thing. It happens all the time. We (single moms) have all encountered men who tell us they want to settle down, be in a serious relationship and have a family. But what we find is that these men, living their bachelor lives to the fullest, are the least likely to actually walk the walk. It is, on the contrary, the men who don’t profess their willingness to settle down so blatantly who truly have their heart and head in the right place.

But because every single mom has encountered a bachelor like you, we thought you could take a moment to explain – for all of us single moms– one little thing?

Are you just wasting our time? If the answer is no…please, clarify:

Do you really think you could give up that spiffy bachelor pad, all of those beautiful women, all of those fabulous nights out on the town, and devote yourself to a single woman and her child?

And please, you owe this to us, since both of us have stayed up way too late and let our kids entertain themselves just to answer your e-mails.


Ms. Single Mama and Single Mom Seeking

[Photo credit:]

{ 18 comments… read them below or add one }

liz March 25, 2008 at 5:09 pm

I can’t wait to hear his reply!


mssinglemama March 25, 2008 at 6:35 pm

So far … not a word. Random? Where are you?


Jim March 25, 2008 at 7:25 pm

I did. At the time I met my now ex-wife and her son, I had two other dates set up with non-moms, which I cancelled.

She was so refreshing! Like moms here have said, she didn’t play games, we were both up-front with each other. And we had 10 great years before it started going south…

But I digress. If I were a single mom, I’d look at the guy’s family life growing up – was it stable? What are his parents like? Does he have a good relationship with his parents? Was he ever involved in clubs or organizations that promoted family and/or good moral values? Did he help raise siblings (given that he is not the youngest)? And if he was the youngest, or an only child, stay away. They’re used to being babied.

Just some thoughts.


mssinglemama March 25, 2008 at 11:39 pm

Jim – tks so much these are all really good questions. Not sure about the youngest sibling theory but you might be on to something there. How about this – watch out for men who like to be babied – period.

The last thing I need is another person to take care of! : )

So everyone … Single Mom Seeking and I are a bit concerned because Random has not responded to this post or to our e-mails encouraging him to take it lightly.

Do you think this post is out of line or unfair? I think the letter is actually quite flattering…it’s coming from two single moms who rarely throw out compliments to single men. And we are also saying that we are definitely intrigued and charmed … so … what do you think???


Jim March 26, 2008 at 1:13 am

Eh, he might be workin’ ya. Was his message to you delivered in a “Hey, bay-Be” sort of way? Meaning, is he looking to get a little?

Posting the same thing in two different FORUMS is one thing, but sending the same PERSONAL message is another.

Or maybe he’s just consistantly stating his position.

I’d also stay away from guys who are too much into their own looks. Fashion models don’t – necessarily – make good fathers.


Cara Hurley March 26, 2008 at 6:52 am

Hi ladies,

I have probably been reading Random E. for roughly as long as you have (maybe shorter).

I have had the pleasure to chat with him and have email correspondence with him, and take it from me, he is genuine.

His only fault is that he is too charming, but can you blame him? His parents/role models raised him well. He has respect for women and that is such an endearing trait these days.

I may be the only one who saw this right off the bat, but I read him in seconds and came to the conclusion that he shares one very troublesome trait with me and that is of the ‘harmless flirt’.

He likes attention.

He likes LOTS of attention.

From women.

Is that such a bad thing? I don’t know exactly what he was telling you in his email, but you can be sure that he drops compliments left right and centre because he really sees the good and amazing in people, and he does not feel the need to withhold expressing such honest sentiments.

He may have been sexually interested in both of you, curious about single moms etc., but can you really blame him for liking BOTH of you? After all, birds of the same feather flock together. “Show me your friends and I will tell you who you are”. This is what I feel, that both of you are more alike than you realise and he is probably attracted to the quirks shared by you two. It is your similarities afterall that made the two of you such good friends, is it not?

Another reason he might have been dropping the same line is because he is a lawyer. They learn very quickly to copy and paste 😉 It does not mean they don’t mean what they copied, it just saves them time.

He’s a good egg.

I am only typing out this reply because I have been on the receiving end of similar suspicious questions by people wondering about my intentions because I am such a lifelong flirt it does not even occur to me that I am flirting anymore. I flirt with men (and women, although I am straight) all the time. The point I am trying to make is that I love flattering people and all the comments and compliments I make are always genuine.

So, our Esquire could be engaging in just a bit of ego boosting harmless banter or he could be seriously sexually flirting with you, but they don’t have to be mutually exclusive now, do they?

Of course, I could be totally wrong… 😉



PS: If I’ve not made much sense it’s because I suffer from insomnia and am in the middle of an episode right now. It’s almost 7a.m. and I have not slept since yesterday.


Cara Hurley March 26, 2008 at 6:55 am

PPS: For the record, I don’t think he is remotely good looking. From the way he writes, he comes across as an average looking guy, maybe leaning towards the ‘plain’ side.

I’m not usually wrong about such things 😛


missmegs March 26, 2008 at 11:46 am

Wow, I don’t read your blog for a few days and look what I miss!


mssinglemama March 26, 2008 at 12:53 pm

Jim and everyone else…he didn’t send us the same e-mails, just the same overall messages. And the black book line was repeated but yes, Cara, you’re right. If there’s a good quick way to deliver a message – why not use it twice.

And yes, he was just harmlessly flirting with us and we, for the record, were harmlessly flirting back.

I kind of feel like everyone, including Random is missing the point. This is about single moms.

1. Unfortunately we don’t really have time to flirt even if it’s via e-mail.

2. It occupies our mind more than it would the average woman. A random prince who is perhaps interested can be a bit consuming.

3. We were looking for an answer to a specific question and posed this question to Random because every single mom I know has come across the same conundrum.

There are always those extremely flirtatious yet intellectually charming guys who get under your skin but aren’t really on any level ready to date a single mom. Why? Because dating us means dating our kids too…not at first, of course, but you know what I mean.

If you’re a single mom this should all be making 100% sense. If you’re not … then I can understand why it wouldn’t.

Dating for us is so much different – hence the entire purpose of this blog.

PPS to Cara. I have to disagree. I think he’s definitely attractive. I would argue above average … but who knows. This is all theory of course b/c we can’t see his picture. Good luck getting some sleep!!!!


Cara Hurley March 26, 2008 at 1:50 pm


I do apologise. Upon second reading, in addition to your excellent explanation above (oh gee, I’m flirting again, doh! lol) 😉 I realise I did not understand the bottomline for you and Singlemomseeking.

It’s about “single moms”, in particular the juicy carrot he dangled over you (ie “the little black book”).

Now for more of my insomnia-induced musings (pay no serious attention please).

What I am getting from all of these is that certain seemingly well adjusted (read ‘too good to be true’) men, sometimes looking for an ego-boost and an ‘experiment playing daddy’ come into the life of a single mom with less than ideal intentions.

Some of these men, sadly, actually prey on single moms because they are lead by the media (and evil pick up artists) into thinking that due to the shortage of men (seemingly) willing to take on the role as father to a child that is not their offspring (or even the responsibility of looking after a ready-made family) single moms are somehow ‘more desperate’ (read easy). And so they come with all sorts of silly empty promises, saying how they want to settle down, have a family etc., whereas all along that is just what they know would…no pun intended….open the floodgates. They could end up using and dumping the woman…scurrying off with their tails between their legs saying “I’m not ready to be a father!” whilst the woman shouts back “my child already has a father, I just wanted a companion who we could trust!”


Perhaps that came out in a really bad way. Sorry.

Anyway, my message to Random Esquire is this: These women obviously did not mean to harm you or shame you or even ridicule you. Not in the slightest. They are only looking out for single mothers and probably feel that they ought to ‘out’ any piranhas preying on the vulnerabilities and sensibilities of single mothers. They are a very different breed in the sense that they come with a very special package that will remain in their lives forever, and these are cherished lives. A child is only with mom for a few years and then they are gone (out into the adult world). Mothers have but a few precious years to enjoy that growing and maturing phase with their children. They have but a few years to shape them up to be upright, moral, law abiding citizens, and it is imperative that these children are protected from the kind of flimsy relationships women without children often enter into without a second thought. The child is usually their number one priority.

If you waltz into their lives dangling all sorts of carrots in front of them, and manoeuvre your way into their childs life…and then turn around and realise you made a mistake, the devastation can be quite epic. Not only would you potentially seriously hurt the mother, but you could hurt the child too. These are protective women, and they don’t like introducing ‘random’ men to their children until they are absolutely sure of his intentions (read: long-term commitment).

PS: Apologies for any typing errors. My errant tomcat was strongarming me for cuddles in the middle of typing this, complete with headbutting my fingers and trying to sprawl himself on my lap and keyboard. He’s such a baby!


Cara Hurley March 26, 2008 at 2:12 pm


I just read your blog entry again and I just had to comment on one of the options you gave Esquire and that is option:

(c) come to terms with the fact that you’re just not ready for single moms and to cease all flirtatious e-mails to us immediately.

I promise after I say this I will leave your blog alone and go and find something else to occupy my frenzied mind.

What I wanted to say about option C is that I really don’t think that is the case with Esquire. I really don’t think its a case of him NOT being ready for single moms.

I think its a case of him NOT being ready for a serious relationship/commitment. Full stop.

He’s just recently come out of a long term relationship. From the way he writes, we already know he’s in touch with his pink 😉 sorry, feminine side. Men like these take quite a while to get over a lost longterm relationship. I had an ex like that and it took him over a year to get over the relationship.

Was he dating before that year ran out? Heck yes, as early as six months after the split. However these were all casual relationships and he made that clear to the women from the get go. Whilst his ego and body were ready for a little lovin’ 😛 and female company, his bruised heart and emotions was not ready to deal with the responsibilities and heaviness that can come with a full-on, committed, monogamous relationship.

And therein lies the problem with Option C.

Perhaps Esquire is ready for a little bit of loving (he currently casually dates) but he is now aware, through the fantastic list titled rules for dating a single mother (I think that’s what it was called, was it?)…that he cannot get that kind of loving from you or any respectable single mother for that matter (read: a single mother who takes her parenting responsibilities seriously, for example NOT Britney Spears).

So yeah, he might be ready one day…who knows? But for now?

For now I think his heart still belongs to Boss, his ex, and until such a time that he reclaims it (which I doubt it next to impossible due to his continuing close contact with her) the only thing he can offer you now with certainty is most likely friendship….and/or flirtatious emails.

Okay, that’s it. I’m done. I’m off to occupy my mind with something else. If you see me back here in less than 8 hours, shoo me away.




mssinglemama March 26, 2008 at 3:24 pm

Cara. I couldn’t agree more with just about everything you’ve said. Thanks for sharing and please try to get some sleep. : )

Well…because I’m a single mom, I’m afraid I haven’t yet mastered the ability to resist the dangled carrots. So I’d rather them just not be dangled. Period.


jon b March 26, 2008 at 4:01 pm

This is a really interesting situation. I consider myself a reformed bachelor so to speak, and I think I understand what is up with Random E. To be quite honest, gaining a woman’s interest, attention, and generating attraction is a skill set. Some men are born with it, some learn. I was never smooth, but the last few years I picked up on a lot of things my friends were doing and incorporated them into my persona. With minor tweaking I had no trouble meeting women and since I was single, I would often have multiple dates in a week, some back to back, some on the same day. You hit a point where it becomes natural and you flirt and attract women intentionally or unintentionally. Plus, it becomes a tool to get faster service at the bank, information from DMV, or a few extra fries at a resturaunt. From that perspective, i can see where Random E could find himself flirting/hiiting on you both.

That said, as much as it is a skill you have, you also have the ability to deactivate it if you so choose. I met my girlfriend and we become very close extremely fast and I stopped dating around or getting phone numbers from “prospects.” There have been a few occasions where I have been out and casually chatting and inadvertently seemed like I was flirting and someone was interested, but it is a choice to or to not act on it.

Make no mistake it is very challenging to meet a single mom and get into a serious relationship in some ways. Going from your bachelorhood to dating a woman with a child requires an entire reworking of your life. You have to look at yourself and see how selfish you are, how easy you really have it, and assume a certain amount of responsibility to be punctual and commit to plans because a single mom’s life is so structured because the child needs it. Canceling a date better be because of somehting nearly cataclysmic because date night only comes around once a month and when mommy has planned and arranged for a sitter it is terrible to have something come up. Not to mention it will bring back memories of the biological parent who failed her and the child again and again.

It is very difficult to walk away from your bachelorhood. There are times you reminisce about the freedom and laugh about glory days with friends. But with a single mom you also have a woman who will appreciate quality time with you, who will love anything you do to help her out, and if true love forms you have the extreme pleasure of bing involved in a child’s life and having special moments that you will never forget. Is it difficult to retire the player’s card…absolutely. But if love forms and you are willing to make osme sacrifices, the rewards far outmeasure the challenge. I was up until 2am with my girlfriend putting together and adventure play system with swings, slide, and a rock wall. The feeling of accomplishment, the smile on her child’s face and excitement as he ran towards it, and the tone in her voice when she said I love you made every whacked thumb, stubbed toe, and trip to Lowe’s worth it.

Conversely, I can’t wait for my next “man night” to get smashed and complain about every second of it, lol. The duality of life, eh?


QTMama March 26, 2008 at 4:41 pm

::sigh:: I love Jon B.


mssinglemama March 26, 2008 at 5:03 pm

Me too. : )


dadshouse March 26, 2008 at 7:21 pm

Ms. Single Mama – if this is really about single moms not having time to date and flirt, rather than being about bachelors who aren’t ready for a family – can I ask what it is about the charming bachelor with the little black book that you single moms find so appealing?

Jon B makes a great comment on men in general – some are very smooth flirters, and do it without trying. In my blog today I wrote about married men who want to be my wingman, and the attention they crave from women. Flirting is healthy, but is sometimes misused.


Ms. Single Mama March 26, 2008 at 7:30 pm

Dad’s House. And that my friend is the million dollar question. Believe me.


Andrea March 26, 2008 at 10:57 pm

make no mistake ms single mama, i completely understood the nature of your question. i can get so consumed with harmless flirting that i’d rather it didnt happen, to be honest. ahh the million dollar question. i’ll never have an answer.


Leave a Comment