How to find love online, one first date at a time

It took 120 first dates for a former Sonoma woman, who is out with a book about her adventures, to find Mr. Right. What went wrong?|

Wendy Newman admits to making every dating mistake possible.

Divorced after 12 years of marriage, she awkwardly belly-flopped into the online dating pool at the age of 35 and found she really didn’t know how to swim.

“I used and ended up draining the pool and moved over to OKCupid, which is where I met Dave,” she said, referring to the high-tech engineer to whom she committed herself in a ceremony two years ago.

But it took 120 other first dates over a ten-year period to finally reach what she hopes is the last.

“If someone had said at the beginning you’re going to have to go on 121 first dates I probably would have cried,” said Newman, 48, who spent many of her dating years in Sonoma County - Healdsburg, Geyserville and then Sonoma - before diving into the bigger dating pool of San Francisco in 2010. “But if they showed me life after the 121st date I would have said OK. I would do it again to get to him.”

It was at date No. 54 that she reached rock bottom.

At age 43 I went on the worst date of my life. It was so horrible and I had learned so many things,” she said. “I realized I needed to write about them.”

That’s when her search also became research. The result is “121 First Dates: How to Succeed at Online Dating, Fall in Love, and Live Happily Ever After (Really!)” (Atria/Beyond Worlds; $16).”

Newman hopes that by passing on what she learned the hard way will help other singles avoid the same mistakes.

She began to look backward as she plowed forward. “I started seeing where I had been great or where he had been great or where I blew it or where he blew it.”

Because she had marked all her dates in her Google Calendar she had a complete record of all of them; she started tracking and deconstructing them and insights emerged.

The date when she hit bottom turned out to be a guy 30 years older than he said in his profile and dressed like he was living on the streets.

“He made me pull conversation out of him all night. He wasn’t really talking. That usually happens when a guy doesn’t like you and he doesn’t have the heart to end the date,” she said. “I just kept trying to pull new topics out of him.” At the end of an the excruciating meal he made a bizarre proposition after running up a large tab he expected her to split in half.

The lesson? “I should have ended that date before it started. But it was just one in many times I stayed when I shouldn’t have. I should never have sat down and asked for a menu. I didn’t even call him on the 30 year lie. I wasted a good two hours on this guy and those are two hours I’ll never get back.”

It’s a lesson Newman, who at the time was running an online vacation accommodation booking service called StaySonoma, could have learned on Date No. 1 if she was paying attention. That’s when she met up with a rancher at McNear’s in Petaluma. Before they were even seated at a table he had downed two whiskeys.

“He told me how I have to give up my travel agency because he needed not only a girlfriend but somebody to run his ranch. But as we were walking to the table I should have said, ‘We won’t be staying. We’re not a fit.’”

That became one of her most important recommendations: don’t waste your time and his, just to be accommodating. “I’m not saying be a mean person. But there’s a gracious way of saying we’re not a fit and slipping away.”

Not all of her dates were disasters. It took her seven years to get to date No. 7, including one guy she stayed with for years until it struck her that the only reason she was staying with him was because she dreaded dating and he was cute. That became another important lesson.

“I told myself, ‘You need to stop doing this. You need to look at a person for compatibility rather than how cute they are.’”

Dates No. 8 to 121 were crammed into a whirlwind of three years; sometimes she went out on two dates a night.

“Somewhere between date 54 and Date 78 I thought, ‘Oh my god. I’m not going to meet my partner. I was discouraged plenty of times. I’d hear all these people saying things like, ‘You have to be at the high vibration’ and ‘get in top shape.’ Well, I wasn’t always in top shape, but I just kept going.”

At some point Newman wound up at a workshop by relationships guru Alison Armstrong, who teaches singles how to understand and communicate with the opposite sex.

She was so intrigued she wound up training with Armstrong, and becoming a relationship coach herself and leading workshops on “Relationships by Design.” In the process she’s interviewed thousands of men on sex, dating, relationships and women, conducted polls, had one-on-one discussions with men and witnessed more than 100 panel discussions. Still, she continued to date, until she hit No. 121.

“It was a great date,” she said. One of the things that made it different was that it was really easy. They met over a quick bite at Zuni Cafe in San Francisco. She was able to draw out stories from Pierce. He was kind and easy. The explored taboo topics and it was okay. What she didn’t do is presume that because he was newly divorced, that he would be a nightmare of unreadiness, like Date No. 60, who she dated for a few months before he bolted and broke her heart.

It was Pierce’s first post-divorce date, her 121st. But it clicked.

“You’ve got to leave room for serendipity,” she said.

Newman’s Top Date-Busting Mistakes

- Leading With the End Game: Don’t confess what you’re looking for in a relationship or life partner on the first date. Lighten up and keep it loose. “For goodness sake, you might as well sit him down and ask him for a pre-nup,” said Newman, who did that more than a few times. “It’s not that the guy may not be looking for the same thing. But for many of them. The first date is just to see if you even like each other.”

- Talking About Your Past And Exes and Complaining: “There were times when I would have to hear the four hour version of his ex-wife,” Newman said. “It’s never sexy. It’s a date killer.’ She remembers one date who spent the entire time complaining about everyone he ever went out with. Others complain about coworkers, their mothers, their jobs. ” Instead, talk about positive things. What you love about your life. What you’re looking forward to. What matters to you. “You can go endlessly back and forth about what you love about your life.”

- Being a Crazy Person About Your Pet: Sharing basic pet preference is OK and finding out if he or she is allergic. But don’t bore them with TMI about Fluffy or Fido.

- Not Showing Who You Are: Be authentic. If you’re looking for someone to get close to, lies or fakery will be disclosed. You’ll also be more appealing to your best match by being yourself.

- Not Posting a Full Body Shot on Your Online Profile: Newman made the mistake of posting a shot of herself sitting, showing off her long legs and cleavage to their best advantage, but hiding her middle. “I didn’t mean to, but I tricked the camera,” she said. She learned her lesson with the date who eyeballed her up and down and then frowned at her. “We had a three hour miserable dinner, he didn’t talk to me, but kept ordering food.”

- Not Being Prepared to Pull Something Out of a Bad Date: Newman became adept at making lemonade out of a lemon of a date, like mining the guy for useful information like recommendations on good places to hike with your dog or the best taco trucks. And if it fails don’t be afraid to double book. She recalls coming home from a bad date at 10 p.m. and finding another prospect online. She IM’ed him and they wound up meeting up for a fun late night date.

You can Reach Staff Writer Meg McConahey at or 521-5204. On twitter @megmcconahey.

UPDATED: Please read and follow our commenting policy:

  • This is a family newspaper, please use a kind and respectful tone.
  • No profanity, hate speech or personal attacks. No off-topic remarks.
  • No disinformation about current events.
  • We will remove any comments — or commenters — that do not follow this commenting policy.