Dating Diary: One Week in the Land of Bumble

We’re excited to kick off a brand new series called “Diaries.” Each week, we’ll take a peek at people’s diaries that focus on dating, money, health and fashion. Whether you want a good example of how someone manages their budget or to simply be a voyeur on a single’s dating journey, there’s something for you. And we want to hear from you, too! Submit your own diary HERE for a chance to be featured on StyleBlueprint. We’re excited to start off with the dating diary of StyleBlueprint’s Marketing Director Megan Casey. Enjoy!

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I’ve technically been single since last October when I ended a nine-month relationship with a guy I’d met on Bumble. After closing his business in Nashville and finalizing a divorce, he decided to clear his head in the wilderness of Canada (which I fully supported) … and then redirect his life by studying for the Bar… in Santa Fe. After letting the long-distance relationship die a slow death over four months, I decided to aggressively Bumble myself out of singledom. The effort is ongoing, and this is an account of one week in my dating life. Grab coffee. It’s exhausting.

*Names have been changed to respect my Bumblers’ privacy.

Monday

During my first date with Mitch in January, he asked me why I was single. Note to single men: Please don’t ask this question. When I answered that I tend to date men who are either emotionally stunted or who don’t live in Nashville, both of which make them ‘unavailable’, he chose that moment to tell me he might be moving to the Midwest for his job in a few months. I have continued seeing him, even after he tossed me that “I’m unavailable” softball. I tell myself it is because I need to keep my options open, but mostly, it is because he is cute, fun and frankly, I am bored. Or lonely, which is often the same thing in the world of dating.

Due to the possibility of an impending move, we’ve kept our relationship light and breezy, never seeing each other more than once a week. This week, our date was on Monday, and we went to Sperry’s to take advantage of their half-price wine deal. Over crab legs and wine, he told me that his boss gave him the option to stay in Nashville; he doesn’t know if he wants to stay or go now. We made stilted conversation through the rest of dinner, but don’t worry, I persisted. We made plans to have dinner at Rolf & Daughters on Friday night to celebrate his birthday (twice in one week, I know). I’ll take unavailable for $400, please.

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Tuesday

On Tuesday, I enjoyed a night off from dating to get together with my women’s group. All of the women are working professionals in media, most of them are married or in long-term relationships; and two of us are single. The conversation inevitably turned to our dating lives, so I gave the requisite updates. Even I’m bored by the never-ending sameness of my love life, so no need to go into detail here.

After spending 30 minutes on Bumble when I got home, I messaged six new guys that I matched with, and three responded. One “unmatched” me after we commented back-and-forth two times, and I couldn’t figure out why. This is a prime example of why dating on apps is frustrating, confusing and woefully impersonal. You need to invest several hours in it to get enough people in the funnel, then one misunderstood pun lands on deaf ears, and you’re immediately banished.

Wednesday

On Wednesday, I went on a date with a new Bumbler to Silo in Germantown. Tyler is charming, self-deprecating and devastatingly good-looking. I’m a little smitten. The one possible hiccup: He doesn’t drink. I’m a bit hesitant to pursue this relationship as I’ve dated men in recovery in the past, and it didn’t work long-term for me. Luckily, he’s not apprehensive about it, and we have a lovely time sharing deviled eggs and ricotta dumplings as I have one glass of wine. The date lasted much longer than I thought possible since we couldn’t stop talking. When the night was over, I dropped him off at his place nearby. In a completely predictable, because-it’s-my-luck turn of events, he lives in the same building as Unavailable Mitch. As I was praying that Mitch wouldn’t see me driving up, Tyler leaned in and kissed me. A tad aggressive, but not entirely unwelcome. I practically pushed him out of the car in my haste to hurry out of the building’s entrance.

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Thursday

Tyler texted me at 9 a.m. to ask me out for a second date. I often worry that I’ve become so jaded with dating that I can’t even get excited about new relationships. I’m happy to report that’s not the case here, and I’m genuinely looking forward to going out with Tyler again next week.

On Thursday evening, I had a date with a non-Bumbler. My brother’s fiance has not-so-subtly been trying to set me up with her neighbor Sam for weeks so I gave in, and we met for dinner at Answer. He was a few minutes late due to a delayed Uber, which was no big deal (plus, he got points for responsibly not driving after drinking). We ordered drinks and an alarming amount of food and got started on awkward first-date conversation. He’s got a Ben Stiller vibe going on and is intelligent, funny and inquisitive. Halfway through dinner, my long-time ex-boyfriend walked in and sat directly behind us, facing me and on a date of his own. I immediately and surreptitiously divulged to Sam that this was happening because I am incapable of hiding my emotions. He quickly made me more comfortable by cracking a few jokes and made sure I was okay to stay. The evening ended well, and I think we’ll see each other again!

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Friday

Mitch and I had drinks at 5th & Taylor and dinner at Rolf & Daughters for his birthday. We had a long conversation about our semi-relationship, in which he shared that he is dating me because he “can’t find anything wrong with me.” It is moments like these when I think about my married friends telling me that I’m too picky. Is it wrong to want more out of a relationship than being with someone who just hasn’t come up with a reason not to be with me yet? To be fair, I’m not head over heels for him either. It’s officially time to end this one … after his birthday.

Saturday

My second night off from dating this week. I spent it at Hathorne with an old friend visiting from New Orleans. We used to share our single dating woes and consult each other constantly. She’s now married and five months pregnant, and I couldn’t be happier for her. She gives me hope that it’s not too late for me.

I got on Bumble after dinner and matched with a cute guy I’ve seen around town before. After messaging back and forth twice, he deleted me without warning. Ouch. It’s the second time this week that happened. Is there a Bumble messaging course somewhere that I can sign up for?

Sunday

To wrap up a whirlwind of a week, I have a first date at Henrietta Red with my latest Bumble match, Mark. He had a subtle, quirky charm about him, and while I wasn’t immediately drawn to him, our conversation did take a fascinating turn, and we took notes from each other on podcasts, books and Ted talks. We got a dozen oysters and he asked for crackers, which was endearing. He asked me why I’m still single (that question again), and I told him that I just haven’t met the right one yet. Somehow, I didn’t mind this question as much coming from him. At one point he proclaimed that we need to be friends, even if we don’t end up dating, and I agreed. A light hug at the end of the night and I’m home in bed by 9 p.m.— my idea of a perfect night.

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For all the exhaustion, tedium and occasional heartbreak that comes with being on the search for The One, Mr. Right and Someone to Enjoy My Life With, I always try to take a moment to appreciate all of the opportunities and new adventures I am having. While I happily welcome the day when I no longer have to field the “Why are you still single?” question, I must admit that it has been a gift to get to know so many kind, open and interesting men along the way.

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