Finally, Lisa Spencer thought as she eyed her latest first date.

I finally hit the dating jackpot.

Spencer, a 30-year-old teacher at Omaha South High School, got divorced nearly three years ago. Since then, she has gone on a first date with a man who showed up wearing gym shorts and proceeded to ogle the waitress for long stretches of the evening. She has gone on a second date with a man who invited her over to his house but failed to warn her it wasn't exactly his — Mom and Dad greeted her from the couch when she walked in.

She had gone on 40 dates total, many of them awkward and a few so horrific that they made her alternately convulse with laughter and consider quitting the Omaha dating scene altogether.

But wait: Date 41 was looking good. This new guy wore nice, date-appropriate clothes. He seemed willing and able to carry a conversation. He sported a nice beard. He actually offered to pay.

Everything about Spencer's latest date seemed perfect, until the moment when he reared back to laugh and opened his mouth wide.

Oh no, Lisa thought, her heart sinking. Oh, oh no. His two front teeth. They are ... gone.

“Call me superficial, but I just can't date a guy who is missing his two front teeth,” she says. “At least explain it to me! What happened to them? Where did they go?”

Friday is Valentine's Day, our annual celebration of coupledom, red roses and overpriced three-course meals. Today, let's consider those among us who are looking unluckily for love. Let's speak of the unspoken difficulty of finding a man or woman in Omaha, particularly when you cross the age of 30. Let's crunch the numbers and show that when the magazine Marie Claire recently named our city one of five “Best Cities for Single Girls,” it maybe missed a thing or two about relationships in the River City.

Let's boil it down to Lisa's simple question: Where did they go?

“The biggest thing for me in Omaha is that the dating pool just seems a lot smaller,” says John DiMartino, a 32-year-old who has lived in Washington, D.C., and Kansas City. “I don't know why, but every time I go out, I can just tell.”

Census data do indeed show that the Omaha dating pool starts shrinking right after college, and gets smaller still by the time you hit the big Three-Oh.

Omahans no longer marry young, like our parents did. But in our late 20s we speed-walk down the aisle, so much so that 60 percent of us are hitched by the time we reach 30.

That appears to leave roughly 24,000 Omahans who are single and in their early 30s, but the actual dating number is likely much smaller.

For example, many of the single women in their early 30s — the women in John's potential dating pool — are in serious, monogamous relationships. Others are interested in women.

The dating pool also gets shallower if the dater chooses to drain some of the water. For example, if you only want to date someone who holds a two- or four-year college degree, then you have just eliminated roughly half your potential first dates.

Both DiMartino and Spencer have taken to online dating sites to try to meet people. Some of these websites routinely match him with women living more than an hour from Omaha. And when they do match him with someone in Omaha, it doesn't always go well.

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DiMartino's re-creation of a recent Omaha online date:

Him: What do you do for work? Her: Meh, I don't really want to talk about it.

Him: What do you do for fun? Her: Watch TV.

Him: Cool, what shows? Her: I don't really follow shows, because I'm on the Internet at the same time.

Him: Oh, what websites do you like? Her: (Shrugs)

“She literally had absolutely nothing she was passionate about,” DiMartino says. “I'm just looking for someone who is passionate. It doesn't have to be their career. It doesn't have to be their hobby. Just something, anything, that they get excited about.”

The frustration of both Spencer and DiMartino is tied to the notion that they might find it easier to meet someone if they lived somewhere other than Omaha.

Spencer remembers how easily she met people while in college at Iowa State University. And DiMartino, an information security specialist who travels in his work for a Fortune 500 company, can't believe how many more single people there seem to be in other cities.

Again, there is some proof to back up this belief.

In the 30-34 age group, 45 percent of women who live in Chicago or Atlanta are single. Approximately 44 percent of women living in Kansas City or St. Louis are single. Nearly 41 percent of Denver women are single. In Omaha, only 38 percent of women in that age group are single, census data show.

There is also an anecdotal sense that Omaha is not a particularly friendly place for single people. When DiMartino goes out, he sees mostly couples and groups of people who never interact with each other. It's much easier to meet a stranger in a D.C. bar, he thinks, because the people in that bar are more open to that experience.

As an experiment, Spencer tried to go out by herself once and see if anyone would strike up a conversation. Fatal mistake: She did so during a Nebraska football game.

On that day, the Cornhuskers trumped conversation with the single lady sitting on a barstool.

“I didn't anticipate how difficult this would be,” says Lisa, who is juggling her dating life with her job, shared custody of a 4-year-old and her classes in a Creighton doctoral program. “Most people I work with are married. Most friends I have, their guy friends are married. This is hard.”

Luckily for John and Lisa, there are two beams of light beckoning at the end of this pre-Valentine's Day darkness.

The first positive is demographic.

The size of the Omaha dating pool actually stops shrinking in the mid-30s. Why? Well ... divorce.

And then the dating pool actually expands as more single women come into the pool starting in their 50s.

Why? Well ... because of the life expectancy of men.

“So you are saying that by the time I'm 60 I'm going to be a hot commodity on the dating scene?” asks John when I inform him of this.

OK, that didn't work.

But wait, there are two other reasons for hope.

It's John and Lisa themselves.

They both admit to moments of frustration while dating in Omaha, but they also have found moments of joy. Lisa has written wickedly funny and insightful things about some of her worst first dates. John dated a Lincoln woman for a while, though they ended up parting ways because of their different locales and career paths.

They say they will keep logging on to online dating sites. They say they will keep going on those oft-awkward first dates.

And they vow to keep looking for that special someone, this time with the clear, mature eyes of 30-somethings who know who they are and with whom they want to be.

“I hope I never stop looking for that spark,” says John. “That bit of passion you find in a new, exciting relationship. ... I'm holding onto that, for sure.”

Says Lisa: “It just takes one. If I go on the right date tomorrow, with the right person, it makes all of it, all of those crazy dates, totally worth it.”

The right person is out there in Omaha, Lisa thinks. He's smiling. And when he does, she will see every last one of his teeth.

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