Super how this story was(Spoilers)

All that happened was, that Harold White, when he was a freshman in high school went to try to take Annie to a homecoming dance, & it wasn't a just the two of them date, but it was them & several other people including Schneider.

Harold never saw her again until some years later, when her sister Claire & Brother in law Steve, went to see him as a client to him. Harold was an accountant including working on peoples houses. He was a freelance Accountant self employed but had enough clients to make money.

He got reunited with Annie when her sister Claire invited him to come to her daughters birthday party, that Annie planned. Annie was an out of work party & event planner at that time staying with her sister & brother in law.

So in a way he was reunited twice, first at the party & then at the restaurant she became a waitress(Annie) making not much money including the tips. He offered her a ride home & told her he couldn't get a girlfriend when he bombed out with online dates or dates other friends fixed him up with & except for clients he was socially afraid and shy some of the times.

His friend he plays golf with told him to go to a dating coach & also told him to approach Julie who passes him by at that other coffee bar, but he was afraid to make his move.

Now Annie had difficulities of her own too. She didn't do any events for a long long time(except for nieces birthday party), & Claire thought she was just freeloading there for a long time after 4 months. So thats why Annie got the job as a waitress working with Kim, who knew Harold as a regular friendly customer. So she needed another job & Kim suggested that she could be Harolds Dating Coach.

Harold tried that other agency that his golf friend recommended but they wanted ripoff prices so Annie offered to do it for a very reasonable price & in a personal way too.

Plus her 8 lessons of some that had free extra credit were working perfectly for him & as she was giving him these lessons & he did land Julie after all, over time, he was starting to feel loving vibes again toward Annie.

Annie however could never get any steady boyfriend(even with the tons of dating experience she had) but she was able to help Harold in many ways.

Things were going well for Harold & Julie but they didn't end up permanently together because, they didn't have alot of things in common like, Julie didn't want to do slow dancing in Harold's home nor was interested in romantic music oldies & she didn't care about going into the woods either for him to photograph but she did it just to compromise. Usually in relationships you do negotiate & compromise, & give into each others interests some of the time, however, while Harold was with Julie on the latest dates, all he could think about was Annie, even though she was only doing things with him as his private coach. Plus Julie later on didn't have the vibes either even though she liked him at first.

However Julie did help Annie Out when a friend of hers needed an event planner plus at that event where Harold & Annie were finally in a permanent relationship with a slow dance, Annie got other offers for event planning & maybe even for private dating coaching as well.

So what you learn from this movie is sometimes overtime even though it wasn't meant to be you can fall in love with that person overtime for real.