I am not alone…real dating horror stories

I cannot report that I’ve been super enthused about my post-divorce dating experience. I’ve experienced flaky men, very little chemistry, awkward conversations and have met online one man who sparked my interest enough for me to genuinely look forward to seeing him again. As it happens, I’m not the only one going through an unsatisfying streak…

I recently enjoyed a morning with a younger, single (never married) girlfriend who is beautiful, fit, charming, delightful, intelligent and far beyond kind. She is the kind of girl a man would be proud to bring home to meet his family and, if he wasn’t a complete idiot, might recognize that he should throw himself at her feet and beg her to spend the rest of her life with him. And soon, before some smarter man figures it out. She is that amazing!

And she is having as shockingly bad experiences (or bad luck?) as I’ve been having on the dating scene…actually, worse!

I “get” my problems dating. I still feel like a fuck-up some of the time. More-like-it suggested I’m judging harshly — and I know I’m finding excuses to not get out and meet men. I’ve got baggage and am still working to become the kind of woman who draws spectacular, loving men to me effortlessly. And, frankly, my time is precious and so are my girlfriends. I’m more inclined spend time with them than take a chance on meeting some other guy from an online dating site.

But my girlfriend? Well, her time is precious, too, and she’s got an active social life with lots of great gals. She is the girl who taught me to meet men with a camera: go up to a group of guys, and ask one of them to take a photo of you with your girlfriends — it’s an easy ice breaker and great way to start a conversation.

Here are some of the dating stories she told me during our time together:

She met a really awesome guy out one evening. They hit it off immediately and began talking, texting and spending time together. Suddenly, he didn’t call for a week. And then, when he did, he told her that his ex-wife (from whom he’s been divorced for eight months) wanted to get back together. Though she treated him horribly and initiated the divorce, he was compelled to give it another try because “it’s the right thing to do.”

With another man, she had amazing intellectual and philosophical conversations (not to mention some amazing make-out sessions)…until that night he told her he could really imagine spending his life with her, thus felt the need to lay his cards on the table. Dude is creeped out by buttons and fascinated by skeletal parts of small animals. Rarely wears suits (in fact, chose a career to accommodate) and collects the remains of small furry animals. No shit. Needless to say, her attraction evaporated pretty much on the spot. No more for me, thanks; I’ve lost my appetite.

And then there was the long-distance man she so enjoyed over the phone and via email…when they managed to be in the same city, he took her out for a lovely dinner and then suggested a walk. But before they went walking, he had to stop at his car so he could strap on his hand gun. What?! Ok, he was in the military and from a more dangerous part of town…maybe forgivable…until he began telling her this story: from his apartment window, he heard a scream and looked out to see a man dragging a woman across the parking lot forcefully by her hair. He yelled at this man to leave the woman alone. The man told him to mind his own business. So he began assembling his semi-automatic assault rifle right there in the window, aimed the laser at the abuser’s head and cocked it… Wow! Gotta love a defender of women, but you could dial 911… or you could whip out your semi-automatic assault rifle, right?

And there’s more!

She went out for lunch along the river with a man she’d met. At the restaurant, she ran into the proprietor (who she knows). Her date immediately said, “Great, I hope now we’ll get a decent table and not have to wait so long!” He also connected with her on LinkedIn and, within minutes, proceeded to make sales calls to her place of business. Ewww. She later learned this fellow is a notorious jerk with whom several unfortunate, but fabulous, women have had run ins.

I can’t claim to have had such fantastically bad luck as my girlfriend…yet, apparently these are not unusual stories among singles these days. Another girlfriend has shown up to dates who looked nothing like their profile photos — I mean they were outright using someone else’s pictures. One guy was of an entirely different race than his online photo! Just goes to show you, there are a lot of nut jobs out there…

What are your dating horror stories? I’m dying to know. Honestly, in the same way that watching The Real Housewives makes me feel grounded and serene, it makes me feel just a little less alone in this crazy dating world to know others are experiencing a little madness, too!

on developing dating clarity

Earlier, I wrote: “The brilliant thing about failure is that, with time, it brings about great clarity. It is because of the experiences I’ve had — my failed relationship, my attainment of a mediocre position in my career — that I now know more clearly than ever what is truly and deeply important to me. I have a fairly well-developed grasp of my own strengths and weaknesses, and have discovered what makes me feel whole, fulfilled and alive. I am grateful for these lessons learned.”

I am grateful for the lessons learned, but I find myself laughing at this sense of clarity I seemed to have for a moment in time. Refining one’s sense of self, sense of other and desires all seem to be ongoing processes. Perhaps at that time I had a great vision for what I didn’t want, and maybe that felt like clarity to me then. It’s the knowing with certainty which direction to go, which next steps to take — in relationships and career — that is the challenge.

Long ago, maybe even before my ex moved out, I began a list of qualities that I’d like to find in a mate. In truth, I probably began developing my list in a somewhat reactionary manner, including the many of the desirable qualities my ex lacked. Or any qualities in direct opposition to those he possessed. Whatever.

As time went on and I began to see the beauty in the world again, I saw more wonderful qualities to add to this list…

And then I worked on myself and spent some time acknowledging what I know about me and what I need and what I know I want, and I added more to the list…

By now, I have a pretty clear picture. Yet, I continue to meet, interact and spend time with men to keep refining and adding clarity. And, though I have silly notions about what kind of car he might drive or what clothes he might wear or how tall he might be, I do genuinely recognize how little importance those things carry. The substantive stuff has to do with the way he thinks and carries himself through this grand life journey.

In other words, I’m listening very closely to the language he uses and how he expresses himself, observing his manners and witnessing my own feelings when I’m in his presence. Most of my list is about truly noble qualities, rather than external factors such as looks or cars or career or income.

My dating experiences continue to inform this list, especially as I consider the type of man who might integrate into my little family. And I think this is particularly true of men with children. For example, I went out with one cute, quirky, computer geek who has twin boys who are younger than my children, one with ADHD and the other on the autism spectrum. I could see loving a man like this. I could even see welcoming challenging children into my heart. But I would likely view trying to integrate such a bunch into my mellow family as too disruptive to my own children. So add that to the list…

My last post was about resonance and dissonance — the things that we can vibe with or not. The thing is, I have a pretty broad, open mind. And I often allow myself to be talked into things. But I know what I like, what resonates. And if you try to persuade me to go out with someone who’s not a match, I’ll probably be convinced to give him a chance. It’s just that in the end, I usually find out that I was right to begin with.

kissing frogs

When I try to explain to some men that I don’t plan to date one person exclusively for awhile, they nod with understanding and wish me well “playing the field.” Meanwhile, they explain, they’re looking for someone special… as if these are two different things.

How many times have we heard, “you’ve got to kiss a lot of frogs” by the time we’re adult women?

I am looking for someone special. But to find him, I recognize that I’m likely going to have to meet and interact with a lot of men. I don’t plan to fling myself into exclusivity any time soon. But that doesn’t mean I wouldn’t veer that way if it felt completely natural and right. After all, I am a monogamist at heart.

It should be said that as many of the men I’ve met online interpret the same messages to mean that I’m ready to get serious and, because they’re not, they opt out.

Am I sending mixed messages? I’m using the same words. But, if I’m honest, the energy behind them is more than a little inconsistent.

which is worse, hormones or tmi?

I’ve mentioned before that the 40-year-old divorcée’s libido is beyond compare. I had a few months of fun as a singleton and then decided I was over the empty, hollow physical affairs. In other words, I’ve given up casual sex in search of meaning.

But I can’t deny that lately I revisit this stance at least monthly, if not weekly. (Okay, fine, perhaps daily or hourly is more accurate.) Depending on where I am hormonally.

Again, this topic is inspired by someone I met online — or, rather, the kind of information to be found online. I liked his mind, yet I don’t anticipate seeing him again — at least not in a romantically inclined manner. Still, having had some rather openly expressive conversations and flirtatious emails, I found him sexually intriguing. He seems more experimental than most of my past lovers have been. He obliquely mentioned porn twice in approximately three conversations, as well as confessing that he’s a big fan of toys. I can’t deny having browsed through all the sex-related questions he answered as part of his profile on our dating site. It seems he has answered an abundance, compulsively…and the things he’s willing to do with his tongue are…well, let’s just say the thought excites me.

In other words, I probably know too much for my own good. I can’t help but think it would be fun — really fun — to take that knowledge and convert it into experience.

Thus, in spite of my desire to have a tender, loving, intimate relationship with genuine companionship and long-term potential, my hormones and intrigue are conspiring against me. I am actually tempted to proposition this man. Even though I know better. Even though there are many other guys who have shown far more interest in getting physical with me, rather than merely titillating banter. But, Jeez, while I’m searching for the needle in the haystack, is it really necessary to deny myself some healthy sport?

The problem is, of course, that while I’ve proven to myself that I am capable of sex free from emotional encumbrance, I think the likelihood that I could manage such an arrangement with this particular fellow is small. Who was it who observed that men can’t think clearly until they get sex, while women are capable of thinking clearly only until they have sex? At any rate, I definitely think there’s some truth in it. I’m inclined to believe I might develop feelings. So I shall try to resist the encouragement of the devil on my shoulder.

I’m not really sure whether it’s hormones, this blessed, cursed 40-year-old libido or too much graphic knowledge that’s causing me to have these thoughts. But I’d be lying if I tried to deny thinking them.

that’s more like it…or not

I wrote a several days ago about more-like-it, who I met at a coffee shop a few weeks ago. I’d met him online, then in person, we’d talked on the phone, and I was enjoying getting to know him and his flirtatious personality.

When we first communicated, the conversation and flirtation flowed naturally. He was articulate and we seemed to be of a similar mind. He said all the right things. When we first met, I learned he had studied Japanese in university. I had lived in Japan. I was looking for someone who had bandwidth, presence and was concerned with health. He talked about balance, engaged parenting and cooking with organic ingredients.

I confess that physical beauty matters to me (I am a Libra, after all), and I’d give more-like-it a solid eight on a scale from one to ten. In the world of our online dating site, however, he’s a 26 (yes, out of ten) — far and away the best match for my physical type that I’d met (not only because of general attractiveness, but also because he could easily be assumed to have sired my offspring).

Finally, previous to meeting more-like-it, my most recent emotional attachment had been to Chi-guy. I wondered where all the guys like him — articulate, attractive, creative, intelligent and so much more — were in this city. Sure enough, more-like-it shares both age and astrological sign with Chi-guy. (Both are Virgo goats; neither an auspicious match for me.)

At the risk of being redundant, so much of what I’d put out there on my list, what I want — both written and unwritten — and more was reflected back at me. Though I doubt I’m explaining it very well, what I experienced was like some bizarre universe communion, a cosmic call and answer. I felt validated. And kinda powerful.

More-like-it was emotionally expressive and warm, yet I sensed there was something holding him back. His pain was palpable — too fresh for his divorce timeline. Following our last lunch, during which I asked him what he wanted (he said he wasn’t sure he knew), he spent some time reflecting and realized he wasn’t ready to date. So he dropped out.

I can’t deny feeling a little disappointed. I could feel a definite intellectual connection and was beginning to sense a physical connection, but we hadn’t built that emotional bridge yet. This was a pretty rockin’ guy, with a lot of positives going for him. The thought that I might get to know him better had given me something to look forward to.

More-like-it had solid, compelling reasons for taking a couple of steps back and away from dating. And I took a pause myself — I cancelled a date or two and left some messages unanswered for a few days to re-evaluate my own readiness. (Suddenly my profile seems to be on fire!)

He told me that I deserve to meet someone amazing and spend time with people who are “all in.” Yet some of his reasons for backing off are the very reasons I’m staying in. I’m looking at things differently these days:

I’m meeting people because I enjoy meeting people (even when I don’t really feel like meeting people).
I’m flirting to practice flirting.
I’m dating to develop confidence in relating to men romantically again.
I’m taking what I can from each interaction, trying to give and receive something positive each time, continuing to develop a clearer picture of what makes me feel good and what a life-affirming relationship looks like for me.
I’m not “all in” myself. And I may not be until I fall in love. “All in” suggests commitment to me, and the only commitments I have right now are to myself, my children and to putting myself out there.
Even if I’m only 85% ready to date, dating casually is what’s going to get me ready. Learning to take the small disappointments in stride is the fuel I’ll use to both toughen up and open my heart.
Who can say they’re ready for a serious relationship? You’re only ready if you find someone who inspires you to open your heart, take risks and be fearless. And that happens over time.
Although I ultimately want marriage, I don’t expect the guys I date to know what they want right away — and I especially don’t anticipate they’re going to know whether they feel something special for me for a long time. They may use dating to develop clarity, too.
I feel vulnerable putting myself back out there, but facing my fear and challenging my beliefs is exactly what I need to move forward right now.

Yes, the human heart is fragile and it’s unfair to mislead anyone. But if we’re authentic — even if that means admitting uncertainty — it’s not misleading to discover, learn and grow in relation to others. In fact, most of us are doing these very things every day. And I have learned something from every single date I’ve been on.

So, while I’m a little bummed that I won’t be spending time getting to know more-like-it better, I’m going to add some of his amazing qualities to my list. I’m going to use having met him as evidence that great guys are out there, in this very city! And I’m going to ask the Universe to give me more of that cosmic “call and answer” dance — it will make putting myself out there all the easier.

my online dating scare

I’ve written a couple of earlier posts about online dating (here and here).

I was ambivalent about venturing online. I still had some feelings of attachment for Chi-guy, I wasn’t sure what I wanted yet, and one of the reasons I was determined to online date was to have something to write about here, on failedatforty. Based on some of the stories I’d heard from girlfriends, online dating was sure to be a content-rich endeavor. (Take, for instance, that guy who messaged me last night asking if he could be my bitch… Dang, I wish that interested me!)

Meanwhile, I’ve worked very hard to develop some clarity around my vision of life, family, the sort of work I’d like to create, and the sort of mate I’d like to attract. I’ve worked on my list to become more and more specific. And I’ve employed the Law of Attraction and meditated to open myself to energetically attracting a man with these qualities and much more. (I mean, I plan to employ my other assets and look my best, but I want the next one to be drawn to my spirit and my soul.)

Just when I was beginning to think that I was in the wrong place (i.e. free site) to meet men — in fact, a group of girls who know what I’m looking for had just told me that I was “sooo eHarmony” (really? me? isn’t that kind of a Bible-thumper site?) — I spotted a few interesting profiles. One, in particular, popped out at me because of the fellow’s sheer genuineness — and yet, there were aspects that made me question whether he was the typical [insert name of upscale-community-from-where-you’ve-met-entirely-too-many-arrogant-players here] douche.

I might have winked, we exchanged a few messages, and I took a chance and suggested that I’d be willing to meet for coffee.

Tangent: Long ago, I had a roommate who would notice an attractive man in public and exclaim, “Way to go, God!” I mention this because…

We met for coffee, and I assumed we’d have an hour or so to feel each other out, determine whether we wanted to see each other again, etc. We ended up talking for more than an hour, found much to chat about, discovered agreement in philosophy in many facets of life and seemed to enjoy each other. I found him pleasing to my eyes, yet felt no chemistry whatever (which is okay, right? …it’s even better if it builds slowly over time). He walked me to my car, gave me a warm and lengthy hug, and bid me a good day.

I got in my car and did a “Way to go, Universe! … that’s more like it!” He was the first guy I’d met (on the site) that fell within the range of my type, a combination of characteristics so unusual I wasn’t sure it existed (in one person) in this city. I could visualize going out with him again without having to convince myself to keep an open mind.

From there, I went home, worked out and rejoiced in knowing that all the effort I’d been putting in to creating was working. And now I had evidence that there are men within the range of what I’m seeking who live here. Directionally, I was getting closer to attracting what I want.

And that scared the shit out of me! Sure, I would love to meet someone really amazingly special this year (as I mentioned while discussing my vision board), but we’re only four months in to 2011 and I wasn’t sure I was ready for special — or even intriguing — yet! So whether he would become someone special or not, I needed to prepare for special… I spent the next week hitting Debbie Ford’s Spiritual Divorce harder than I had before, actually doing the exercises and working to heal, forgive and release any karmic connections that might still be holding me back.

It dawned on me that, while I had listed in detail the kind of mate I want to attract, I had failed to create a list of the qualities that I planned to bring to a partnership. So I began a list of the characteristics I want to embody to be an ideal partner to my ideal mate.

I also went back online and got real about my profile: I made it clear that my ultimate desire is marriage — a true partner and co-conspirator; I changed my ambivalent answers to some questions, such as “How long do you want your next relationship to last?” to “the rest of my life;” and more. In some ways, I feel I’m asking a lot — after all, it’s not just me, there are three of us. And the special man I will ultimately draw into my life will be a loving and engaged father to my children, as well as husband to me.

So what next? Well, I met the more-like-it guy again, enjoyed his company and looking in to his brown eyes, and I was definitely feeling a little chemistry, too. I hope to see him again. I’m not sure he knows what he’s looking for…so it’s too early to tell whether it might go anywhere. I’m also communicating with and meeting other men, learning from my interactions, getting clearer about my desires, and creating space for the possibility that the “or better” may manifest in my life…which, in this time of personal expansion, is ever-changing and allowing more.

Will this guy — or anyone I meet online — be the one? I’m going to take things day by day and focus on opening my own heart, allowing myself to feel vulnerable and soft, and living authentically, rather than try to predict the future.

See my next post on more-like-it.

conjuring the cougar #fail

Yesterday I went on a date with a man I’d met online. I use the term “man” here loosely; he was 26.

We’d been emailing back and forth and texting for a couple of weeks. When I told him he’d have to pay my sitter if he wanted to see me on the days when I have my children, he asked when they weren’t with me. I should have known better then. We talked for a few minutes the other night, and I didn’t find his voice particularly pleasant. I should have known better then. He asked if we could change the agreed-upon venue to someplace more convenient for him — and then chose a bland, American restaurant over something more adventurous. I should have known better then.

But he has his pilot’s license, is wrapping up an independent film that he co-wrote and produced, and is working while finishing an engineering degree, so I thought I’d give him some credit for having the maturity to achieve some goals. And the prevailing advice about how to meet men seems to suggest I should step out of my comfort zone. (Never mind that the prevailing advice about marriage suggests that I should lower my standards…)

As I was driving, probably half a mile from our intended meeting space and precisely one minute before we were to meet, he texted me, “Are you still coming?” I should have turned around then.

My misgivings proved true. He talked a pretty good game for a while but, in the end, he had come from the gym wearing workout attire — I mean the kind that looked sloppy, rather than the kind that highlighted a buff bod. Conversation was forced, until we got to the topic of flying. He seemed like a little boy in hoping to win the Sugar Mama lottery. He still had acne. He actually asked me how I wanted to handle the check at the restaurant. This baby was neither hot enough to coax out my inner cougar nor mature enough to hold his own with an intelligent, cultured woman. No wonder all of his photos were of him inside the cockpit of an airplane wearing a headset — he was insecure even about his looks.

Clearly, the perspective from which I write suggests that I have some expectations. Youngsters — aw, heck, men of all ages — if you want to conjure the inner wild cat (or even get a second date), take note of a few of them:

Dress to impress. I may wear jeans on a first date to keep it casual, but my clothes will be clean and well-chosen (i.e. you’re likely to see a little cleavage), I will have showered and put on make-up, etc. At 26, this baby should have known to put on some flattering jeans and a nice shirt rather than show up in sweats.
Come my way. If you’re asking me out and we’ve already agreed on a location or neighborhood, don’t change the venue with the express purpose of making it more convenient for yourself. Demonstrate that you want to spend time with me through your willingness to meet on my turf.
Be accommodating. If I tell you sushi is my favorite food, either be willing to try something new to please or impress me, or offer an appealing alternative. I get that not everyone likes raw fish, but any urbanite who’s left their home in the past decade knows that sushi restaurants offer a lot more than fish, raw or otherwise — and rest assured, I can point out several options on a menu for carnivores. If that’s still scary, there’s a lot of ground to cover between Japanese and an American burger joint.
If you asked me out, you’re picking up the tab. Duh!

So, after all this, what’s my takeaway? Well, there are two:

First, lesson learned: follow my gut and say no early and often. Date no one who I could not possibly imagine being my equal or an example to my children.

Second, re-examine and clear whatever energy I’m putting out there to attract men who are not in my league. This will take some real work (and may merit a post of its own).

a few lessons in online dating

I’ve had an online profile for a little over a month now, and I’ve learned some things along the way that surprise me:

First, I was surprised at the quality of men I was seeing, largely because many of them were really quite unattractive. Still, I found someone nerdy cute enough to correspond with and decided to keep an open mind.

When an opportunity popped up for me to learn which of my profile photos was most attractive, I took it and was, in turn, asked to compare profile photos from men across the site. I learned which photo was recommended for me to use as my primary profile photo and, later, received some surprising news: I had been deemed — based on men across the site comparing my profile photo against others — more attractive than average, and would now be shown more attractive matches. Really?!? The surprise was not my own relative appeal, but that this blasted online site had been holding out on me, leading me to believe that most single guys were unappealing as hell! Thankfully, I’m now finding there are some men who are both single and good-looking!

Second: People are flaky. I mentioned before that I’d had a date and a second one planned, but nothing further has panned out with that fellow. His life seemed to be getting complicated before communication dropped off altogether.

I’ve been targeted by some guys who simply stop writing after a few messages or can’t hold a conversation, one guy who “needs” a woman, and a few who are all about whether my photos are current. And there are men who haven’t invested the time to fill out their profile or answer compatibility questions, meanwhile expecting me to give them the time for coffee. Some haven’t even uploaded a photo — and I tend to assume there’s a reason for that!

Third: You’ve got to roll with the positive feedback. It’s nice to hear that I have a beautiful smile, whether or not I’m interested — I’ll take it! There is a really cute guy I’d love to meet because he seems like a fun conversationalist and a good flirt. And now I’m being chased by a 20-something. I am mildly amused and flattered by this, and he seems young and eager and willing to do all the work.

cheap sex? on my terms

Slate recently published an article called Sex is Cheap: Why young men have the upper hand in bed, even when they’re failing in life. The article, written by a man, is based on research and data from around the world.

My colleague and 20-Nothings author, Jessie Rosen, followed up with her astute commentary here.

And still I think it’s worth exploring whether the equation changes as we get older, specifically for single women approaching or into their forties. First, let’s acknowledge that, by this time in life, some things have changed for women:

Our libidos are more active. While men are alleged to peak in sex drive at 19, women’s libidos allegedly peak at 30. I say allegedly, because most women I know would argue that we’re even more libidinous at 40. (And because I’ve experienced 50-year-olds with as much energy as any 19-year-old.)
For many of us, sex is no longer about our biological clock and securing commitment, DNA and a provider for our children. Many of us have already met that need, more or less.
We’re more confident — this means being more comfortable in our bodies, more assertive about getting our needs met, more able to be direct and more able to walk away (after all, by this time in life, we’re likely to have acquired more toys — a.k.a. The Elite Sophisticate, Doc Johnson or simply BOB, for Battery-Operated Boyfriend).
We’ve gained a lot more relationship experience, whether we’ve been married and divorced or not.

So…is sex still cheap? A quick look at the dynamics on online dating sites or in any bar will assure you that, yes, sex is still cheap . Men, it seems, are able to find willing partners whatever their station in life. As are women.

But, based on my own experience and some anecdotal evidence from my contemporaries, the balance of power has undergone a nuanced shift: the women I know who are serious about seeking a mate date multiple men — and they wait to sleep with any of the serious contenders. They’ve learned a thing or two about how to develop a relationship and they know that sex can complicate their emotions when they’re exploring whether someone is right for them. Instead, they enjoy steamy liaisons with a hot guy who they’ve already concluded is Mr. Wrong.

By forty, most single women can walk into a bar, pick up a man, take him home, sleep with him and forget it. And they can communicate to men they really care about that they’re looking for commitment and not willing to get sexually involved without it. They know how to respect themselves and, thus, demand respect from a man. (And if you’re a single woman and this doesn’t resonate with you, you’ve at least got to admit to having learned enough to know what you’re getting in to.)

The implication for men at this juncture in life is that, especially if they are finally looking for a life mate, the tables may have turned. If a woman sleeps with a man right away, it could very well be a relationship death knell. It may mean she’s already ruled him out.

second date fail

I reported earlier in the week that I was to go on a second date with someone. We were to meet for brunch at a quaint bistro.

I drove there, parked and went into the restaurant. I thought I saw my date turn in to the lot as I gave the hostess my name, table for two. Strangely, my date did not come in for several minutes. Perhaps he was on the phone, I thought. When three minutes turned into five, I thought I must have been mistaken. At ten minutes, I ordered my breakfast and continued to read the newspaper.

Only after breakfast (remember, I quit my job and have yet to replace my mobile phone, and the restaurant did not have wi-fi) did I get the message that his ex had been called in to the hospital (hmm, a doctor?) and he had to rush back to pick up his children.

So…

What is a girl to do with this? We were about to have a second date. The first was an hour-long coffee two weeks ago, followed by some flirtatious emails. So let’s first establish that there is no relationship — it feels like a very low-stakes situation to me. And if my ex called and needed to be at the hospital, I would have done the same thing: gone home to fetch my children.

Still, because they could come to bear if ever a relationship were to grow, there are two rather critical questions that come up in a situation like this:

How hard would you work to communicate? Guy (not his actual name) knew I didn’t have a mobile phone, but he did know I’d have my laptop. Of course neither of us would have guessed the restaurant didn’t have wi-fi…doesn’t every coffee or breakfast place these days? There is also a city-wide wi-fi program here, but I don’t subscribe to the service. Guy sent me an email from his iPhone while in the restaurant parking lot (I later learned). He could have come in; he could have called the restaurant — in other words, he might have done more to ensure that I had truly received the message. As I said, the stakes were low…but hey Guy, how bad do you want it? Ultimately, if positions were reversed, I’d like to think that I would have had the courtesy to stop, walk into the restaurant and personally let my date know that something urgent had come up. The email wasn’t a total fail, but he could have done better…I say this not knowing whether his ex is an emergency surgeon or a nurse or an IT staffer or a PR person. Which leads me to…
How do you manage an ex? Among my wide network of friends, I’ve had several who are in the second wife / stepmother role. Having discussed these challenges before, the consensus has typically been that — more than being second wife or stepmother — the most difficult role is that which must deal with the ex-wife. The ex-wife can work to sabotage the relationships both between husband and new wife and with the children. If the man in this situation doesn’t have firm, well-defined boundaries with his ex, it’s hell on the entire family. But, according to my friends, the second wife / stepmother rarely gets very far when trying to address these dynamics — she’s often accused of being jealous, not wanting her husband to spend as much time with the children as he does or having other nefarious intentions. None of these are true, but they can appear true to a man who doesn’t see how manipulative his ex-wife is being or is generally unwilling to manage the situation. It sometimes seems that men respond with more empathy to an ex (perhaps out of guilt?) than to the current wife. In other words, ex-spousal management is critical to the health of any individual’s boundaries, and becomes even more important if one is to endeavor to have other relationships. Did my date manage his ex well? Not particularly. But there are still too many unknowns to determine how big a fail this is. First, let me say that Guy alluded to his children having some behavioral or development challenges, which may make it difficult for him and / or the ex to leave them with a neighbor or friend at the last minute. I have no idea how long Guy has been divorced. I have no idea whether the ex-wife wanted the divorce. I haven’t seen any history or patterns as it relates to this behavior.

So here’s what happened afterward:

I waited about a day before I responded to Guy’s emailed cancellation / apology. The tone appeared to have prioritized his “poor me” feelings over his “I am so sorry” apology, but it’s difficult to get a real read over email. My note to him said simply, “you missed a great breakfast — and even better company.”

He replied quickly, expressing his embarrassment over the situation and some suspicion that he had been manipulated or his plans had been sabotaged — along with a compliment or two.

I later replied, “perhaps you shouldn’t tell your ex when you make plans with a beautiful woman.”

Again he agreed and added compliments.

I clearly have the upper hand and can elect whether to see him again or not. In general, he seems decent enough, and flirts articulately. His profile shows cute personality. He is a sucker for The Sound of Music, as am I, and we seem to have a wide variety of shared eclectic interests. I have a mild interest in hanging out…yet I don’t like being yanked around. So I’m really on the fence here…

What would you do? One fail and he’s out? Or give him another chance?