Matt was out in the Hyde Park neighborhood playing tennis with a friend, Jared. Jared had played some tennis in his youth but was struggling to keep up, in Matt's opinion. Matt thought pretty highly of himself regarding his tennis abilities. Right when Jared was about to call it a day, Tyler, a pretty number, showed up, with a neat Wilson tennis bag for her two Wilson rackets, three fresh cans of Wilson, US Open edition balls, and very professional attire. Tyler set up shop at the net on the other court. ‘She clearly came here to play’, thought Matt, as he looked at his current partner, who was about to call it a day. Jared likely just wanted to call the match off out of the lopsided score their set had devolved into, but he later claimed he saw Tyler as well, and thought he might give Matt an opportunity to strike up a conversation. Regardless of his motives, Jared left shortly after, and Matt and Tyler were left alone; Tyler, waiting on her partner, and Matt, hoping for a more competitive rally before he called it a day. At park tennis courts, it’s customary, if not proper etiquette, to offer to play with another if both are without their partners. Matt played this card to his advantage. Now this was smack dab in the COVID pandemic, where there was little opportunity, or good reason, to strike up a conversation with a stranger. Tennis happened to be one of the few activities where players could keep to themselves on their respective ends of the court, while still enjoying an outdoor experience with another. Tyler and Matt were clearly there for the same reason. Matt figured they would likely stay on the baseline, quite a distance apart, and hopefully he wouldn’t be overmatched in order to offer to play again at some later point. I mention this context, because Tyler had only ever played tennis once before in her life. Matt and Tyler couldn’t even properly hit from so far apart, and had to move closer together towards the net. Yet, she was not discouraged, and gave every shot her best effort, and always looked to improve; a quality Matt has since realized and admired she applies to everything in her life. The slow and close play (along with her partner Kylee’s habitual tardiness) gave the two a chance to strike up a conversation, and get to know each other. Other than Matt occasionally providing some tennis lessons, I won’t say what they discussed. But I do think it’s special, how all these circumstances, unexpected and expected, led to that exact moment, and their plans to do that sometime again. They’ve played a couple more times, and will do it again in the future, and the score always started at love-all. I know that’s cheesy, but I think a story as cute as this deserves a cute tennis pun.

Matt was feeling nervous, particularly when Tyler told him she was going to ‘explode’ if she had to travel to her family in Pennsylvania for Christmas, without an engagement ring or news of an engagement. The engagement itself had already been a foregone conclusion. What complicated the matter was Tyler, with her attention to detail, knew exactly when the engagement ring would be ready, and what any prolonged absence from Matt would have to mean. When Matt did manage to discreetly obtain the ring and draft a small speech in his head, he had a matter of days to reasonably surprise Tyler with a proposal. They both agreed they would want the event to be private, and Matt took Tyler to a nearby garden and gave his speech. Tyler said yes, and their dog, Indiana Jones, thought that all this was a fantastic idea.