Hermione had a hard time with relationships. Finding the right one just seemed impossible.
She and Ron had lasted the longest of them all, possibly, Hermione thought, because she simply didn't know what they were missing. They had been the ultimate school sweethearts, Mrs. Weasley had started planning their wedding as soon as the dust had cleared from the war. It took another two years before Ron had proposed, not wanting to waste any more time before they could step into suburban boredom. That had been the very moment in which Hermione realised quite how bored she was already, and that was without the four bed house and average five red-headed children Ron (or more accurately Mrs. Weasley) wanted. It had taken a total of three hours to break the news to Ron. Hermione was sure she had repeated herself at least 200 times within that time span. They had ultimately parted as friends, for which Hermione was ever grateful. Some jealousy had persisted in Ron, but Hermione was convinced that that would have been the case even if they had never hooked up.
From Ron, Hermione looked for a more exciting relationship, and appropriately began dating her boss. At this point in her life, Hermione was interning in the Magical Law department at the Ministry of Magic and at first, when Simon had started sending her somewhat flirty memos, she had ignored him and protested on ethical grounds. After a couple of days, Hermione had pondered how much excitement had been missing from her relationship with Ron, impeccable logic had entreated her to understand that a forbidden relationship with an older man could be the key to her happiness.
Naturally with this logic the whole thing had ended in a disaster. Hermione had been right about the excitement, it had been truly exciting at the beginning, not a dull moment. It began with a flirtation, a sparking romance, and a massive secret. All very exciting and quite alluring to a girl in her early-twenties and her first job. The secret had broken after a few months, and about a month after that Hermione was bored, and quite alarmed at how she had ever found this man, and his nightly floss routine at all attractive or that is was even remotely appropriate that he had begun the flirtation in the first place.
Five months and a swift career move later, Hermione took a different step in her love life, and found a lovely muggle boy with a brand new grad job at a big bank. This turned out to be an even shorter relationship than the last. The boy was perfectly nice, but Hermione turned her head towards her career. Nice boys didn't have the same allure as promotions. Plus she got pretty sick of Ron's sharp jokes about her ever failing love life.
After this, Hermione fell quite in love with a sweet witch who worked on the reception desk at the ministry. It was somewhat of a fleeting romance, and quite delightful. Ending abruptly when the witch's fiance walked in one night, just when Hermione was discovering the true meaning of life. The receptionist got married a month later – Hermione didn't go to the reception.
Whilst all this was going on, and somehow in between her relationships, Hermione attended Harry and Ginny's wedding alone, incidentally having a week long fling with one of Ginny's quite distant cousins. He wasn't even a red-head. A few months after the wedding, they were looking through the freshly developed photos and Harry had noted that he was actually the bar-staff. Hermione, quite mortified, promised herself a lot more care in the future.
Hermione stayed single for a good few years after that, deciding that she was most definitely suited to the single life rather than any kind of dating scene. Being single unfortunately meant putting up with snide jabs from Rob about being a spinster after he had reconnected with Lavender Brown and they had married within a year. She was approaching 29 when Ginny began to get quite worried and ferociously began setting Hermione up on blind dates with every eligible bachelor in town (and a visiting Italian, who Hermione didn't quite mind so much about as the others, though his accent was unintelligible). Whilst Hermione knew Ginny may have had the best of intentions but it did leave her feeling a little sour towards dating in general.
It was on her 29th birthday that Hermione began to consciously question her anti-dating stance on life. And that perhaps, despite Ginny's best efforts, she just hadn't met anyone interesting.
Draco Malfoy invited her to lunch.
A work lunch that is. Not exactly romantic. They had ministerial work to discuss and Draco had suggested that they might as well enjoy a pub lunch while they were at it. No point in starving.
It was the most interesting conversation that Hermione had had with anyone in quite some time and despite some prevailing school prejudices, by the end of the lunch hour, not a scrap of work had been done, and Hermione had a pleasantly warm feeling in her chest. School prejudices didn't last very long when the conversation was that good.
It took a few more work lunches for Hermione to convince herself that she wasn't going mad. It took an exceedingly long exchange of letter for her to allow Draco to cook her dinner in his London flat.
A further three months went by before she conceded that they were in fact a little more than merely workmates and she, somewhat reluctantly, invited Draco to attend Harry and Ginny's anniversary dinner.
Slowly, but with continued persuasion from Draco, Hermione allowed herself to be pulled into the most whirlwind and exhilarating romance of her life. They took to travelling once a month, enjoying the sights of Europe and Asia thanks to Draco's unlimited funds and pull with the ministry.
Hermione spent her 30th birthday at the top of the Eiffel Tower. For the first time in her life, truly happy to have a man at her side.
A month later, in a small little English pub, just around the corner from the ministry, Draco proposed with a delicate diamond ring.
Hermione decided that whilst working was very rewarding, and being single had been just perfectly fine with her, she would never regret that first work lunch. It was also a handy way to eschew Ginny's continuous blind dates.