Fun Online Dating Stories

Fun online dating stories are sometimes hilarious and sometimes heartwarming. Dating in the worldwide online dating scene can lead to some serious long-distance relationships. Even when you can choose guys and girls only in your immediate area, sometimes you’ll find the perfect match on the other side of the country…or even the world. This is one of those internet romances.

Online Dating Success Stories

This is one of the most amusing “online dating success stories” I’ve come across in my entire career. It involves helping people find true love online in a day-to-day basis. I’ll call this one “Olivia’s Story”.

Olivia was in most ways a normal American woman who lived on the in Oregon on the west coast. After having been married for 10 years and divorced for 3, Olivia decided to look into dating online. After all, pickup lines from guys with alcohol breath can only take a girl so far in life. So Olivia, who happens to be a friend of mine I know very well, decided to try out the online dating scene.

Joining the Online Dating Community

Fun Online Dating StoriesOlivia joined all of the most popular online dating sites, making a serious commitment to her online dating journey. Some sites Olivia joined as a free member, while others she joined as a paying member. Also, she didn’t join them all on the same day, but gradually, over a few weeks, if she got bored with one, she joined another.

Full disclosure should be given here. Olivia, the girl in our story as you recall, was a professional blogger, so online dating memberships equal tax write offs. Keeping that in mind, it’s no surprise that Olivia joined eHarmony,,, Yahoo Personals,,,, and even Despite this rather large investment in time and money, Olivia found little worth appreciating in the companionship department.

Online Dating Stories – A Free Second Chance

For a pro blogger, life expierences often equal income opportunity. After spending such a long time with online dating services, Olivia decided to start up a new blog detailing her more interesting encounters and miserably failed experiences. Unfortunately, Olivia was unable to post a single, personal success story. There were some fun dates. She’d made some great friends, but nothing great happened during her virtual dating experience, until…

One day, with no successful matches at one particular online dating service, the company offered her a coupon for “$20 Off On Southwest Airlines” if she extended her profile preferences to be matched up with suitable online daters within a 120 mile radius of her location. Olivia decided, “Why not? Twenty bucks for a profile change! How often does someone offer to give you that kind of free cash?”

Sure, it was obviously a marketing scheme on behalf of Southwest, but with nothing to lose, and future Las Vegas vacation plans, Olivia made the switch.

Romance for a Jaded Blogger

She went on to explain that if she cannot find love within an hour’s drive of Portland, which contained approximately 7 million people, why shouldn’t she expand her horizons and increase her odds of finding a soul mate in the online dating world? “Heck, with my discounted airline fee, I could up my matching distance to 1200 miles!”

Yes, Virginia, There Is Online Romance

She did just that, she ended up meeting a man from Virginia, of all places — about as far away as physically possible within the United States. Shawn from Virginia could be described as a southern gentlemen. Like Olivia, Shawn was also a recent divorcee. Shawn had three almost-grown children, while Olivia had 2. The two met the first time in Oregon, staying together in a little vacation rental on the beach.

For the week Shawn was in Oregon, they slept together without having sex. He held her until she fell asleep, for what Olivia called a “hearts eternity” in the mornings. Shawn and Olivia walked on the beach. They ate together. They explored Olivia’s state together.

A Single Woman’s Realization

Olivia had raised her children on her own. She’d stared down the gas man when he came to shut her heat off. She’d created a successful business all on her own. Olivia had sent a child off to a university already. With her past several years in mind, Olivia felt that the week with Shawn was nice, but she didn’t really need a full time man in her life.

When the time came, Olivia took Shawn to the Portland International Airport and saw him off. Their first couple weeks apart flew by like a breeze, with so much to catch up on after a week rendezvous with Shawn. Of course, the two kept in touch online and talked regularly on the phone, but it wasn’t until about a month later that Olivia realized she did want a relationship full time. She wanted a man at home with her every night, someone to cuddle up with on cold nights. Olivia wanted someone she could wake up to and kiss in the morning.

Olivia and Shawn Realize Their Love

Olivia didn’t know how Shawn felt about this or how to approach the subject with him, so she kept it to herself for some time. About 6 months into their long distance relationship, Olivia received a bouquet of flowers with a sweet little note. The note had a time and the name of her favorite restaurant on it. Giddy about the surprise, Olivia quickly got ready. She walked through the doors and who was standing there, but her “southern stallion”. Olivia was so happy to see him.

Although they talked on the phone every day, there wasn’t a quiet pause for some reflection. The two talked over dinner about everyday events. Eventually, Shawn broke into the conversation and asked Olivia what her plans were for New Years. Confused with the question, because it was early in a new year already, Olivia told him she didn’t have any yet. Shawn then got down on one knee and asked, “How about you make me the luckiest man in the world”. He opened a ring box with a huge diamond in it.

Of course, Olivia said yes. Although in the beginning Olivia thought her cross-country relationship was just for fun and Shawn was someone to get together with every now and then, their romance turned out to be so much more. Olivia is the epitome of a strong woman, and thanks to a Southwest airlines ticket and an online dating website, she now had that strong man that would let her be a strong woman by day, and a willow needing protection by night.

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