First Dates That Will Make You Believe in Love Again

While the laws of relationships dictate that most first dates will be meh, there are those rare ones, often once in a lifetime, that change everything. Here are five first date stories—some magical, some awkward, all romantic—that led to marriage.

Shayna and Alex on their second date

The Low Expectations, Minimal-Effort First Date
Shayna (38) and Alex (41)
First Date: August 2006 in New York, NY
Married Since 2014

Because neither Alex nor Shayna were paying subscribers to the dating website JDate, they were unable to message each other’s profiles. So in an act of what Shayna calls “internet stalking before it was a normal thing,” Shayna Googled Alex’s screenname and discovered she could write him via MySpace. After an initial phone call, he invited her to meet him at a free Yelp event for regular reviewers. “I was jaded by internet dating by then, so I figured we should do something simple and I can peace out if it’s weird,” Alex says.

Alex was 30 minutes late to the event, held at a slider restaurant, but Shayna didn’t mind. Neither of them were looking for anything serious and according to Shayna, there were a “bunch of cute guys from Google around” that she should could distract herself with. When he finally did arrive, his outfit, which included the then-popular MBT workout shoes, made her wonder if he was worth waiting for. But then they started talking…and talking….and talking. “[We were like] an old Jewish couple from the moment we met,” Alex says. They ended up at a bar where they discussed politics, religion and family, aka “everything you are supposed to avoid on a first date.” Their goodbye that night was kissless, but as Alex watched Shayna walk down the subway in a pair of white jeans he “remembers well,” he knew that wouldn’t be the case for long.

Debra and Sandy when they were dating (left), at their daughter’s wedding (right)

The First Date the Led to a Very Quick Engagement
Sandy (73) and Debra (64)
First Date: April 1977 in Los Angeles, CA
Married Since August 1977

Debra and Sandy met by the pool at University of California, Los Angeles, on a sunny spring afternoon. He didn’t ask her out on the spot, but left so smitten that Sandy soon looked Debra’s number up in the phone book. “I was sitting and sewing a quilt when he called,” Debra says. “He said he really enjoyed meeting me and that he had a hectic month ahead, but wanted to go out after. Then he suggested I give him a call in a few weeks. ‘When hell freezes over,’ I thought to myself and hung up.”

A few weeks later, after realizing Debra wasn’t going to call him, Sandy reached out and invited her to go for Chinese on Wednesday. Debra had a good time, but didn’t think it would go anywhere. “He seemed too serious, and too old.” Nevertheless, she was intrigued and invited him back to her apartment for some Grand Marnier, a bold move in the late 1970s. “I was impressed by that,” Sandy remembers.

That Sunday they went to a French restaurant and when she returned from a quick trip to the bathroom he declared, “I am going to marry you.” On Monday they were engaged “and were never apart another day.”

Stacey and Peter at their wedding in 2008

The First Date Between Old Friends
Stacey (51) and Peter (37)
First Date: February 2007 in Minneapolis, MN
Married Since August 2008

Stacey and Peter met in 2005 through the Minneapolis theater scene. They “hit it off right away,” but because of their 14 year age difference, Stacey believed “there was no way we would ever date.” So they became good friends and each other’s platonic “plus ones” for nearly two years.

Then, in January 2007, Peter told Stacey he had feelings for her. Not wanting to unnecessarily complicate their professional relationship or friendship, they spent a week talking through the possibility of dating before deciding to go for it.

On a Friday in early February they went to a movie theater in downtown Minneapolis to see “The Last King of Scotland,” which “isn’t a romantic movie but somehow made sense” for their first official date. When they arrived at the theater the movie was strangely delayed. They would soon discover why: Jerry Seinfeld had rented out the theater for a private screening. When the comedian exited the theater Stacey, completely comfortable being her goofy self around Peter, got behind Jerry and silently “danced like Elaine.” Still, despite their long friendship, the date still felt different. “Finally, we could hold hands, and make out in the car,” Stacey jokes.

Simone and Haley the night they met

The “I’m Never Getting Married” First Date
Haley (30) and Simone (41)
First Date: October 2010 in San Francisco, CA
Married Since 2013

When Haley and Simone met they were hardly an ideal match. Haley, then 23, had recently moved to San Francisco and was just looking for fun. Simone wanted a real relationship and swore she wouldn’t date anyone under 30. But chemistry is chemistry, and they ended up exchanging a memorable kiss at a party one night, one good enough to convince Haley, who “had never understood kissing until that night,” to ask Simone out.

On their first date they went for a weekday lunch at a nondescript Vietnamese restaurant, Simone’s pick. She didn’t want anything romantic because she was planning to tell Haley that she wasn’t interested. Haley, completely missing Simone’s cues, spent the lunch going on and on about how “she wasn’t interested in monogamy and never, ever wanted to get married.”

Simone ended the lunch feeling conflicted. She wanted to end things, and yet she didn’t want the lunch to end. So she asked Haley to grab a martini across the street, where she was planning on gently breaking the news to her. Over a chocolate martini for Simone and an ultra-dry gin martini for Haley, Simone explained herself and, to her surprise, Haley was “very mature and understanding.” In fact, so mature and understanding that Simone began to reconsider things. “She kissed me and things were basically unstoppable from that moment,” Haley says.

Bryan and Tina three decades after their first date

The Cross-Cultural Blind First Date
Tina (51) and Bryan (55)
First Date: January 1989 in Los Angeles, CA
Married Since 1990

Tina’s sister had tried setting up Tina and Bryan on a blind date for a few months, but Bryan was reluctant. He wasn’t sure about dating a Mexican girl, worried that culturally they wouldn’t jive. “He probably thought I had long dark braids and rode a burro,” Tina jokes. It was only after Bryan’s uncle met Tina at a family event and gave his endorsement that Bryan decided to go for it.

For their first date, Bryan picked her up at her mom’s house, where she was still living at the time “like a good Mexican girl.” Bryan found it “old-fashioned and charming.” Tina remembers his outfit – an unfortunate mix of yellows, blacks, reds, and grays that convinced her he was color blind. (He’s not.) She also recalls the three hours of conversation–completely devoid of small talk questions like, “How about the weather? How about the Lakers?”–in a booth at the Cheesecake Factory.

When they got back to Tina’s house and were bidding adieu, she said goodbye Mexico City-style: with a kiss on the cheek. Bryan panicked. He was unaccustomed to this tradition and, in the moment, had no idea how to respond. He “patted Tina on the back,” and then said, “Take it easy.” They both went to bed that night worrying that they blew it. Nevertheless, Bryan didn’t give up. He checked in later that week to inquire about a school project Tina was working on, and then asked if she wanted to go to a movie that weekend. Clearly, she said yes.

Most Recent

Latest Full Episodes

Create a Profile to Add this show to your list!

Already have a profile?