Dating in Boston

So here I am, sitting in a restaurant by myself, drinking a glass of Pinot Grigio.

No I did not get stood up by a guy. That would have made this post that much funnier though. I actually was “stood up” by some people I planned a little get-together for. I am obsessed with this podcast – Almost30. The hosts, Krista and Lindsey are these amazing humans that created this pod when they were in the weird transition before you turn 30. They have since passed the golden age (30 I am talking about) but continued to grow this community into something pretty incredible. I was able to get involved as the Ambassador for the Boston group. It has been such a great way to get to know people out here and expand my friends list.

Anyway, it is my duty as Ambassador to plan at least one event a month for the members of the group. Tonight was drinks/dinner before checking out this light art exhibit thing in the Seaport. We were going to meet at 5:45. It is now 6:21 and I am almost done with my first glass of wine…waiting on another.

Side note – I haven’t had ANY wine this week. I started this gym that I am obsessed with and am really watching what I am putting into my body. 2020 is my last year in this Saturn return thing I am going through – essentially, I have until December to continue “learning lessons”. FUCK – I am SO done learning lessons. More on that later.

Ok, second glass of wine in hand. I have no ill feelings about the lack of attendance. SHIT HAPPENS. Seriously. It is actually a blessing in disguise because I am now writing. I haven’t done it in so long and am wasting a good web domain. What I am sharing with you today is that fact that dating in Boston is so hard. Like reallllly hard.

I broke up with my whatever he was (since apparently there were two of us for a solid 70% of the relationship) in November. This was the guy that I was planning on marrying – the one that I have written about before. Yea, that shit, I mean, ship, has sailed. He is dating the other girl now if you are wondering. Still a little bitter. But if you ask ANYONE who knows him and what has transpired between him and I the last 5ish years, I definitely have the right to be. Don’t worry, I deleted his fam and friends so they won’t be reading this. And honestly, I am doing really well. Enough so that I downloaded both Bumble and Hinge a few weeks ago. I wanted to put myself out there again.

SWEET JESUS. Why did I move to Boston!? Kidding. But seriously. My “type” is not the New England folk – or at least the ones that are on the free versions of these apps. Which is probably my problem? Hopefully?


This is the one where the woman has to message the man first. I had high hopes since I have no problems initiating things. And since you can’t message until you match with the other person, I figured there was some interest on their part. Well let me tell you, not the case. First of all, I probably only matched with like 20% of the people that I swiped right for. Which means 80% of the people I would like to connect with, don’t want to connect with me. This legit does not hurt my feelings. I know that I am freaking awesome, seriously. Of course it would be nice if the guys I was attracted to were attracted to me but such is life. Of the 20%, I think I had 3% message me back. And the conversation – or lack there of – was so boring. Needless to say, I deleted Bumble about 17 minutes ago.

Another side note – is it really that hard to find a tall (over 6’), successful in his own way (I don’t need a doctor or anything), liberal, pretty fit (dad bods are also great), sweet, honest (I am fucking DONE with the narcissists, duh), extroverted introvert with midwestern values, who wants to be the best dog dad and not have any biological children?!? Yes. The answer is always yes.


This is the one that EVERYBODY told me to partake in, and I do know quite a few people who have had success on Hinge, so I decided to give it a try. My pics were pretty great. I definitely showed my witty personality. And yet 0%, yes you read that right, 0% of the men I commented on (again you can’t message unless you match with the person) commented back.

Third side note – here is what I remember my profile to be. “Minnesotan in Boston – basically the nicest Masshole you will ever meet. Pretty basic chick – obsessed with my dog, sarcastic, love to travel, LOVE my coffee…and then my wine. Into concerts (mostly country), sports (mostly hockey) and dive bars.” I am on glass three of wine now so take that with a grain of salt. But DAMN. I am a chick I would want to date!

I will also share that I deleted Hinge about 7 seconds after Bumble so I can’t go back and look. No one. NO ONE responded to my funny comments. Again, this doesn’t change my mindset about myself. I am still a badass chick.

It does make me wonder, though, who these New England guys are. I have heard that Boston is not a great place to meet someone and that all the good ones get swopped up real fast. I don’t recall the exact reasons why they said it was tough out here, but I am finding that to be true.

I did a little test while I was still on Bumble with my job title. I watch Younger with Hillary Duff and her PR BFF told her that guys get intimidated by successful women. She changed her title to “Creative Director” from “Publisher” or something like that and she got so many more matches. I am a Field Marketing Manager for this pretty awesome company and had that up for about 2 weeks. I would say about 5% (of the 20% of matches I got) happened during this time. The other 15% happened when I changed my title to Marketing Specialist.

WHAT THE FUCK. Are you kidding me?! It is 2020.

I feel like I need to just take a moment to enjoy this time in my life. My pup, a new job, lots of travel, new gym, new friends – and of course all my besties and family. Maybe, just maybe, I will meet someone organically? Is that even a thing anymore?! I won’t know until I start actually doing things. Trying new restaurants, focusing on my health, having out with people who lift me up, and getting through the rest of this God-awful “learning” phase of my life.

Dating in 2020 is hard. Dating in Boston is hard. Dating is just hard. Stay strong out there!

The Nicest Masshole > forever single?