Date Reporters

Five Important Lessons From An Actual HowAboutWe Date

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This is the latest post from Helen, our bi-coastal Date Reporter. She’ll be documenting her experience dating in both San Francisco and Boston as she travels between the coasts for work. Catch up on her story here.

When I first starteds a Date Reporter, I did not consider the possibility that someone would find me through this blog and then knowingly try to date me. I always figured it be more of a turn-off. Not so. I guess this takes fan mail to a whole new level.
A couple of weeks ago, a gentleman whom I will refer to as the Writer, clicked on one of my HowAboutWe date suggestions (“How about we… go for a bike ride along the Charles”) and told me he was “Intrigued.” At this point, I need to confess that I ignored his intrigue because honestly what am I supposed to say to that? Give me something to work with! My editor’s told me before that the best way to get a response is to send a direct message, and I guess she was right.

But The Writer must have read my mind. The next day, he followed up with:

“I find very cool that you have a blog… oops, should I not know that? I wish to be a writer one day, it’s nice to see others who actually do it. Would be happy to go for a bike ride, and maybe stop in one of the platforms by the river and watch the sunset :).”

I was intrigued. And flattered. Ok, mostly flattered — they weren’t kidding when they said it’ll get you a long way. Anyway, I’m trying that whole “give it a chance” thing. Not to mention that he looked pretty cute in his profile pictures.

He had another thing going for him: He sent a personalized message. It was great to get a meaningful note rather than one of those copy-and-paste “Hey, how’s it going” or “You have a beautiful smile” messages. Those generic messages are huge turn offs. If you are even remotely interested, show it by taking 30 seconds to ask me about something in my profile.

Lesson #1: Send a Personalized Message.

I think that online messages are similar to texts: if you want a response, ask him a question about himself. Lots of guys (and girls for that matter) don’t see the need to respond if there’s no question posed, so I asked him why he wasn’t writing if that’s what he wants to do.

Lesson #2: Ask a question.

However, I was totally overwhelmed by his second message. Though it was serious and heartfelt, it felt like he was trying too hard to bond with me as a fellow writer. I mean this isn’t a composition competition!

Lesson #3: Keep messages light and short and save the more serious stuff for when you’re trying to woo me in person.

Despite my initial misgivings, I decided to meet up with The Writer because hey, you never know. I soon realized, however, that I made a grave mistake in proposing a physical activity for our first date. A bicycle ride Helen? Really? Sure, to most people, that sounds like a fairly normal and enjoyable date activity, but for me? Let’s just say I’m known as the Sweatiest Girl Around. More to come on that later. But at the time when I posted it, I kept thinking about a nice, hypothetically perfect bike ride followed by a hypothetically perfect picnic with the hypothetically perfect man. Problem is, I hypothetically isn’t reality.

Lesson #4: Don’t post dates you’re not willing to follow through on.

So instead, I skillfully convinced The Writer to meet for a drink at Lolita, an activity that I assumed would be free of any sweat-related humiliation.


How, you may wonder, is that possible? Was it hot outside? Were you actually in the desert and under a blistering and scorching hot sun? No. Of course not. I was perfectly and completely non-sweaty during my pre-date drink.

But despite all these positive signs, I literally had sweat dripping down my face. Dripping. I guess it’s just my body’s oh-so-hilarious reaction to me trying to be a normal, social creature. Fantastic!

Moving on: The Writer came into the bar in the middle of my towel-off. I tried desperately to look cool and dry which was clearly ineffective because at one point he felt compelled to say, “Just breathe. Calm down.” So much for playing it cool.

After I managed to slow the sweat to a calm trickle, The Writer and I had a surprisingly fantastic conversation and covered topics ranging from our jobs to our mutual love for Spain. We talked about both my blogs as well although he was a little weird about how he found me, which makes me suspect it was through my personal blog, Single/(almost)White/Female, rather than this one. I also learned, and was quite relieved actually, that he was European, which is why his messages seemed so formal and, frankly, bizarre.

Although I was having fun chatting with The Writer, I didn’t quite feel that spark, which he unquestionably confirmed later. During our conversation, he asked when I was planning on moving to San Francisco, something I clearly mention in my profile. I was honest and told him that I’m moving in January and am just looking to do some casual dating until then. I didn’t realize how much this affected him until later, when in the middle of an anecdote, he said, “I know you’re not supposed to talk about ex-girlfriends, but since you’re moving anyways…” and continued to tell me a story about his ex.

Excuse me? What just happened? You, sir, messaged me even though you knew I’m planning to move in the near future — my profile clearly reads “Just started new job in San Francisco but in Boston for the next few months” — and now you’re acting disappointed? He even told me he follows both of my blogs, which clearly convey this information. I’m not sure what he expected, but I don’t think I did any false advertising of my situation. In fact, I’m really starting to think my problem is that I’m so upfront and honest with everyone.

Lesson #5 (maybe): Temper the honesty?

I sat there sipping on my margarita, trying to figure out how to wrap up the evening. I didn’t feel that instant chemistry, and apparently he thought I was a waste of time. Fortunately, he gave me an excuse and told me I looked tired and asked if I wanted to go. After he paid for my drink, we got up and walked outside together, still making casual conversation. When we said goodbye on the street, I decided to cut off any potential funny business and gave him an appropriately European goodbye: the triple cheek kiss.

All in all, it was a fine experience although I am starting to rethink my dating strategy surrounding my move. I don’t think I’ll see him again because of the aforementioned reasons, but I’m glad to have met The Writer and to confirm that not all single men are nuts. Sometimes they’re just European.
A New Englander at heart, Helen splits her time between Boston and San Francisco where she’s looking for love, laughs, and the next great burrito. Check out her misadventures at Single/(almost)White/Female.