She smiled.

Here’s the scene: my buddy and I were in a wine bar. There were women everywhere (weird for a weeknight in Palo Alto, but I won’t complain.) Women would strut into the bar in twos and threes looking sexy and confident. I’d try to exchange glances with ones who caught my eye, but they were too busy turning guys’ heads, then acting like none of it meant anything. They’d share a throaty laugh with their girlfriends, drink some wine, get hit on by some tipsy gray-haired guy sitting next to them at the bar, then leave.

Granted, maybe none of these women wanted to meet any men. Or maybe they’re just used to clubbing, where guys approach them like wolves, whether they smile or not. But this was no meat market, it was a wine bar with a more reserved clientele. (That doesn’t mean we’re boring.)

But one woman stood out. She came in and flashed a wide grin, making eye contact. Talk about inviting. As it turned out she was meeting a guy, but it became clear soon enough that they were just friends. More smiles and eye contact later, and my buddy and I started chatting with her.

(Full disclosure: she and her friend were moving from a bar table to a couch, and when she passed by our table, she smiled again, and offered us a cracker from the basket she was carrying. If you were following my late-night Dad’s House Twitter feed, you already know about her Freudian slip.)

I can’t tell you how many times I come across a woman who catches my eye – on the street, in the market, in a coffee house or a bar – and I’ll smile at her, but rather than smile back or make eye contact, she’ll look away with casual indifference.

Is it a game for some women? They do this looking away trick a lot. It’s like they’re trying to avoid eye contact. I’m pretty sure it’s not me – I’m handsome enough, and I’ve seen enough women do this trick with other guys. Let me just say, it makes it a lot harder to say “hi” when a woman is looking away.

My buddy and I chatted Smiling Woman right up. Her friend came over, and the four of us engaged in conversation. By the end of the night, Smiling Woman and I swapped numbers. Since then, we’ve talked on the phone and met up.

Will we be single parent friends? Weekend activity partners? Drinking buddies? Lovers on call? A couple who dates? Who knows. It’s way too early to tell. I’m going into this with no agenda. I’m just glad I met someone so friendly, energetic, attractive, and nice.

I love when a woman smiles.

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But on this particular night, my usual spots were dead, and I criss-crossed town looking for a better option.

When all of a sudden, I saw her.

Across the street was a brown-haired woman in a long black wool trench coat, black pants and heels. She was tall, fit, with an athletic gait. (My x-ray vision sees all.) She completely turned my head. I can’t explain it. It’s one of those in-person things that’s individually unique. Attraction is strongest when it’s simply felt.

I decided on the spot – wherever this woman went, I would go, too. Wine bar? I’d chat her up over Pinot. Dive bar? A watered down g-and-t would hit the spot. Pub? Let’s just say I’m a Guinness man.

She walked two blocks, with me trailing her. Don’t worry, I wasn’t being all creepy stalker-like. I merely headed her same direction, at her same pace.

She ended up in the Peninsula Creamery.

For the uninitiated, the Creamery is an old-fashioned burger joint with shakes and malts and fries. If she sat in a booth, my tailing-her days were over. But wouldn’t you know, just my luck, she sat at the counter!

Dad’s House tip for singles everywhere: when you dine alone, sit at the counter or bar. It’s totally normal for other singles to sit nearby and strike up a conversation.

I sat two barstools away. She ordered a sundae, and I ordered a coke.

At this point, it’s important for a man to say something – anything – to start a conversation. I noticed she was reading the LA Times, which most Silicon Valley people don’t read, so I asked her,

“You from LA?”
She looked over, and said, “Is it that obvious?”
“Your paper,” I said.

From there, we were off to the races. I asked her questions, got to know her. She was in management consulting, working with a Valley firm. She played rec-league co-ed softball back in LA. She loves the beach. She’d been in Palo Alto for a few days, and this was her last night in town. She expected she’d be returning in a few weeks.

I asked if she wanted to grab a drink, and she said yes.

We headed over to a posh Indian lounge, and shared exotic cocktails, and talked some more. We were really getting along. I told her I was a dad. (I’m not a big fan of getting married on the first date, but I do tend to put my parenting-self out there. Then I can talk unfiltered about my kids.) She said she admired that. She was itching to settle down and become a mom.

We moved the party to a British Pub, and ordered Newcastle pints. (Guinness seemed a little heavy at that point.)

Mid-drink, I realized I had a choice to make.

• Try to sleep with her tonight
• Try to see her next time she came to town
• Do nothing, and simply be happy and grateful for her company this one night

Of course, she had to make this same choice, too.

Door number one was most tempting. We were both attracted to each other. And while first-date sex is a terrible way to start a relationship, for a business traveler or a single parent sleeping solo way too much, it can happen.

Door number two was the conservative, nice guy approach. Believe me, if she lived in the Bay Area, it’s the one I’d recommend. But she lived in LA. Who knew when she’d be up here again? Besides, exchanging numbers and good intentions with someone who lived a plane flight away rarely panned out. There’s too much time to contemplate the future. Even if a long-distance relationship was do-able, at some point someone needs to move. And as a single dad involved in his kids’s lives, it won’t be me.

Door number three wasn’t even worth considering. If there’s attraction, I tend to want more.

And here’s the thing. I actually think she was up for a one-night stand. But I wanted to see her again. I opted for door number two. We swapped phone numbers, and shared a hug and a peck at the end of the night.

I called her twice since, leaving voicemail both times. She never called back.

If I had it to do over again, I’d choose door number one.

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Only problem – he wanted to hit a sports bar frequented by Stanford students and grads.

Ugh. I’m too old for that. We’re both in our forties, so he’s too old for it, too. The difference? I have a daughter who will be going to college in just over a year. I can already picture her hanging out in places like this. (And I don’t want her in a place frequented by middle aged men!)

We wandered around to a few other bars, but the sports bar really was the place to be. So, I sucked it up, and we went on in.

Just as I pictured, young people everywhere. Tons of women, too (a good thing). But as we ordered our beers, I noticed something else. Only half the crowd was too young for me. The rest was right in my league. (Now, now. Dad’s House readers will wonder how many hot bus girls there were. I’m talking about women in their 30s and 40s! And they weren’t even lonely housewives.) Just shows you can’t judge a sports bar by it’s cover.

We elbowed our way onto one of the long tables. A couple of women nearby were very happy to have us join in. With a football vibe, it wasn’t hard to start up conversations. I also exchanged some flirty text messages with some female friends who couldn’t come out. (No discreet affairs going on, they’re just good friends.) One of the texting women was a single mom who had her kid this weekend. The curse of conflicting custody schedules.

To make a long story short – we drank plenty of beer, we ate plenty of sketchy food, we chatted with plenty of nice women, and we had a plenty good time.

When’s that Super Bowl thing?

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Still – What a scene!

We got our wine, chatted a bit, then wandered around the bar. A woman pulled me aside and said, “don’t I know you?”

Um…no. (Cheesy pick-up line on her part, but it worked.)

We started talking, and she pulled us over to a table with her girlfriends. They were all attractive, in their forties.

And all of them married.

My buddy and I are both gentlemen, and these women were interesting, so we hung out and chatted for a while. Can you say, Lonely Housewives?

One of these lonely housewives said she hits the bars two to three times a week. A second lonely housewife was totally hot for another guy in the bar, but wouldn’t actually talk to him. She wants to have an affair, but doesn’t want to screw up her marriage. Still, she sent some dirty text messages while we were there. The last of the lonely housewives looked heartbroken and depressed – turns out she’s going through rough times in her marriage.

So here’s the thing – I’m divorced, I know what it’s like to be in a marriage where the love dies out. But these women weren’t looking for nooky. They were simply lonely housewives wanting company from some men. Where are their husbands?

Note to all married people: be happy and grateful you have someone to come home to, someone to sleep with, someone to vacation with, etc. (For those still single, I offer marriage advice from a single dad.) My heart goes out to lonely housewives everywhere, but that doesn’t mean I want to get involved.

If you’re a lonely housewife or out with lonely housewives in a bar, please let the singles mingle with other singles.

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This would be my first Thursday night out in a year.

At 6pm we drove to Palo Alto and hit a wine bar that had recently opened. There were tons of good looking women drinking glasses of white and red. Unfortunately, they all looked 23, and I’m mid 40s. Not exactly at a similar life stage. Still, we enjoyed a flight of Merlot and some crackers and humus, and caught up with each other since we hadn’t hung out in a bit. (He’s a sailing buddy, and we are overdue.)

We bounced to another bar, the Empire Tap Room. An older set, and way too crowded. We headed across the street to a microbrewery, Gordon Biersch. Only one table open, way in the back. We headed to a nearby restaurant with a wine tasting bar. No attractive women. We walked down the street and looked into several new bars/restaurants. Plenty of couples, and hardly any singles.

Francis Ford Coppola’s wine tasting bar was sure to be happening. We went there, only to find the windows papered over. The place had gone out of business. A 60-something couple was standing out front. “What did this place used to be?” they asked. “Coppola’s,” I said. “Damn,” they said. “We were supposed to meet our friends here. Oh well. Can you suggest another restaurant?” I asked what sort of food they liked. “Anything with a bar,” the woman said.

Damn straight.

We trolled by Zibbibo, an upscale restaurant with a nice bar and Mediterranean cuisine. There were maybe four guys and no women. Finally, we headed to Three Seasons, a sister restaurant of San Francisco’s Slanted Door.

Bingo, it was packed!

With guys.

I swear, there were 100 men and only a handful of women. It’s an upscale place, and judging from overheard conversations, most of the men went to Stanford Law. We ordered drinks and appetizers. Where else would we go?

At the table next to us was a total hottie. No ring. Mega eye contact. Sitting with her parents! Can you imagine? I think she was a Stanford undergrad. (btw – I HATE when guys check out my daughter right in front of me. I know she’s beautiful and athletic, even hottie material. But I sure as hell don’t need every 15-50 year old guy checking her out. Like my buddy and I did to the woman with her parents at the table next to us. Doh!)

Our waitress was gorgeous – Vietnamese, slender, definitely enhanced (which is not my thing. But when she’s the only attractive woman in a room full of men, you sort of don’t care.) She was working me and my buddy big time – flirty, flirt, flirt routine. My buddy was convinced she wanted me. I was convinced she wanted a big tip. (Waitresses get hit on 7 times a night, on average.)

A couple of drinks, two spring rolls, one order of sushi, and a bowl of steaming fish with noodles later – we called it a night.

Ah, Palo Alto. That mecca of … horny men? I can’t imagine a more accurate adjective.

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(Dining alone at a restaurant bar is a different story, and is a great way to meet people, be they business travelers or locals who are single.)

The problem is, some married men use their wingman role as a ruse to meet women. Sure, any married person deserves some playful sexual sparring with members of the opposite sex other than their spouse. It’s healthy to flirt. But how much is too much? A married man as wingman can be bad for everyone involved.

• I’ve had married buddies compete with me for a woman’s attention. It’s hard enough to meet people to date, even tougher when your friend butts his head in with nothing at stake.

• I’ve had married buddies charm the girlfriend of a woman I’m talking to, so much so that the girlfriend wants to date him. Didn’t she ask if he was married? Didn’t he tell her? (Some married men don’t wear rings, at least not in bars.)

• I’ve had married buddies’ wives ask me why I kept their husband out so late – on nights he didn’t even go out with me!

Please know that not all married guys are like this. (From my experience I’d say most married guys are not like this.) But some are. They betray their spouses and friends, and smile and lie to the women they meet. (Of course, when a husband watches wife and lover, that’s a different story entirely.)

Why do they do it? Some men are unhappy in their marriages. Some like the thrill of the chase. Some need to feel the spark of sexual conquest. A lot simply need women to love them. They’ll say anything to make a woman think he’s the most fabulous creature on earth, sometimes by simply noticing things about her and helping her feel great about herself. It’s an ego need. (Random pop psychology note: often when a person feeds off the adoration and love of others, they are doing so because they don’t love themselves.)

As for me, next time I’m out I might go by myself. Just don’t automatically think I’m a creep for drinking alone. I might be doing it to help a married friend stay out of trouble. Or at the very least, let him find trouble without my help.

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