My journey through the dating jungle of Boston and looking good while doing it.
The Dates
Documenting the stories of the good, the bad, and the possibilities in dating.
Rules, Rules, Rules!! Dating Rules for 2011
Mar 28th
For the most part I am not a risk averse person, and I also believe most rules needed to be tested broken stretched and rewritten (this does not apply to laws established by government and basic human kindness.) I have come to realize by not establishing or breaking plenty of rules, in the end I am still single. I know it just seems like a game is being played, maybe a little, but I need it to just slow down a bit. So this year I am going to be more obedient.
DatingandDior Dating Rules
1. Less availability
I am busy, I run a t-shirt line, I am pursuing my MBA, and I am always on a coffee run. I will no longer push things aside and make room for you, you fit in where you fit in.
2. Stop texting, emailing, or responding immediately
I know the rule is to respond in however long it takes for a guy to respond to you. He responds to a text 2 days later, you respond to a text 2 days later, but I always say I will respond now and get it over with. No more. Time is a tricky thing, and I will play the response time game.
3. Two hour date maximum
For a person who hates running long distance, I sure do love some 3-5 hour dating marathons. This is way to long. Sometimes they are fun but most of the time they turn tedious. I need to know about you in a couple dates not via over night shipping.
4. Two drink maximum
Most of you know I can drink with the fishes. Am I an alcoholic, nope. I just have a higher tolerance for the good stuff except whiskey two glass max or tequila one shot max. I will reconsider it to one drink in a two hour period, but depends on who is paying.
5. No more new outfits for a new date.
I have an overfilled closet with fabulous wears. I wear one outfit on a date and it never sees the light of day again. I a not spending any money for two hours. Since summer is upon us and my hair does not know how to be straight in the summer, no more blowouts either. I do love my mani-pedis though so that will not change.
Spring is here! Let the dating resume.
Mar 26th
Spring is finally here (even though snow flakes are coming down in Boston) and this hibernating bear is now ready to hunt. I am kinda over the whole online thing especially since I feel too many creeps, assholes, sexaholics, and ,mentally disturbed men seem to find me. Where am I going to find men, couldn’t tell ya.
In reviewing past posts I realize i seem to give the men too much power over the appearance of the date. For instance, when Mr. Game Changer told me it was the best date ever and he got butterfly’s in his stomach from kissing me, these are two emotions I never got. I didn’t walk away thinking it was the best date I just thought it was a good date and actually thought during the date we should have been just friends, and he wasn’t creepy. After the kiss nothing jumped or moved in me at all. I think I continued it because its good to get attention and I thought if I don’t get on board with these feelings I am going to miss out. So I went in heart first, in reality it just never should have happened. Between my instincts and little signs everything was pointing in the wrong direction, but I had to keep going because I didn’t want to miss out, I wanted to be in love again, and I wanted to be in a serious relationship. In my mind I twist and bent as much as I could to make this happen, in reality it was nothing close to it. I know it’s easy to say this in reflection but my friends and family were telling me since I got weird texts during the Christmas holiday to just leave it alone I didn’t and the whole thing went sour immediately.
I digress, the point is I know what I want and I know who I am and I know you can never make a guy fit into anything. I now also realize my instincts are smarter than anything else I got and I have to trust them no matter what. The power begins and ends with me, and shall be reflected from that point here on out.
Update: Mr. Game Changer
Jan 22nd
Since I have no patience on figuring out boys. I sent the following text.
Me: Can you text me Done if you are no longer interested in us and we will both know
Him: Done.
I knew it was going to happen after our last debacle and probably shouldn’t have put the power in his hands but it is what it is and now I can go back to drama with school and less drama with boys. I started looking on match again today prior to this happening so I think I was pretty much done too. He told me before “I have nothing to offer.” I just thought it was the holiday blues. I sent the same text previously but he continued to contact me so I thought it was just the moment, in the end it was just the truth. I know that’s a red flag but maybe I just wanted it so badly I was willing to look over everything to feel something again. Previously, I wrote it would end because of me, but in the end I can say it truly wasn’t me at all. I wasn’t the weak one or the eager one and took my time with it. I didn’t close my mind to possibilities or shut down after the second date. I proudly can say I didn’t fuck it up. I am a better person for the experience. I really don’t feel the need to analyze it any further. Plus I started to identify with the Mumsford and Sons song Winter Winds and the chorus during the winter break.
And my head told my heart
“Let love grow”
But my heart told my head
“This time no”
Date with Mr. Game Changer
Jan 20th
Disclosure: I wrote this at the beginning of December and held on to it, and I couldn’t tell you why. Maybe out of the hope this would actually work out, as Miz Purple told me “You are crazy. You always think things will end. You are crazy.” I will discuss that with my therapist. Honestly, I really liked him and haven’t felt that way in a long time. I had no cynicism or felt he lied about anything. It felt good to know I could feel that way with a guy. He made me feel beautiful without saying it at all. It ended because our schedules were too different and I just didn’t fit in with his limited time, or because of a PMS emotional moment. (It happened and I can’t take it back.) I won’t lie and say I don’t want it to end and parts of me holds on to hope it will magically all work out and I probably won’t move forward till I know it has officially died either way, it is what it is.
During this stressful time of school and school I had time one evening for a date on Saturday. I didn’t know if I should go because of everything I had to do but I was reminded that I needed to balance my life more with this work. I met Mr. Game Changer on match of course. He isn’t my normal type in fact quite opposite, except for the fact he is really tall at 6’3″. He is blond blue eyes and very Bostonian Irish (which I find charming). He winked at me and I decided to write back due to our mutual interest in movies. We conversed via email and text through Thanksgiving break. We finally decided we had to meet and even though I had two group meetings and a presentation to work on I took Saturday night off. Believe it or not with my lifetime of dating (especially online) I still get really nervous. We decide to meet at a bar on Newbury Street at 7pm, and of course I am running extremely late due to wardrobe confusion. On my way there I found my normal nervousness subsided due to actual exhaustion. I was warned by classmates if he is a dud just leave and I made sure I had some back-up plans to get me away.
Once I walked in the bar, I was excited because it was a cute date place. I thought “now this is a place where a first date should really be.” Then I saw him and he was nothing like his pictures. He recently lost weight and looked very nice and actually was casually dressed up (also a nice change.) Then I did something I never do on a first meet and greet date, I immediately hugged him. I apologized for being late and he was a gentlemen by stating it was worth the wait. I order my Blue Moon beer and it begins.
First point of conversation football and his predictions The Patriots are going to the Superbowl, and my prediction they weren’t (I am good at picking Superbowl contenders.) Next topic Lebron James and the coach situation. I think he was very impressed I actually new my stuff and could keep up with him sports wise. We continued talking about career choices then the bar changed from young and hip to Cougartown so we ended up at the Pour House. I told him previously I didn’t like the bar because of a bad date some months back and he assured me it would be different. So I bit and off we went.
I ordered some food and we started talking about music. I told him I karaoke to Bruce Springsteen and he told me he could marry me now, but then I told him I could sing any Garth Brooks song and he took it back. We talked films (both love Unbreakable), and he saw The Town twice I told him I laughed at it. We go to the downstairs bar and all of a sudden I feel I am at a college bar, but it didn’t matter I definitely wasn’t the oldest one in the room. We talked abut everything else in the world and jabbed each other about our accents. I noticed my body language changed. I was leaning towards him and facing him. (I will not believe it is due to alcohol.) Next thing you know it is midnight. I gave myself a 10 o’clock curfew because I knew I had to be at school early the next day. He walked me to the T and we hugged twice. He later sent a text message stating that “that was the best date he has ever been on.” I smiled. He also said he wanted to kiss me but was a gentlemen.
Around 4 o’clock the next day he texted me again and we agree to watch Sunday Night Football at another bar. I realized I was completely exhausted but it gave me a couple hours to whine down. This date was even better. I soon realized all the normal dating stuff was out the door. I didn’t need to worry about holding my tongue or being too brass. He got it and gave it right back. There were no issues this. He said a lot of McDreamy moments that night.
- Me: How much of this game have you watched
Him: I don’t think you realise you have 100% of my attention
- Me: Next semester will be really stressful for me. You caught at the end of the insanity.
Him: That’s ok that’s what I am here for.
Me: I don’t think you get it, I have six classes
Him: That’s what I am here for.
- Me: I am thinking of taking time off when I graduate and I want to go to travel the world.
Him: I will have time off I can definitely go meet you there.
Once the date ended he positioned himself for a kiss. I told him “you really want to kiss me in front of a bar that is so cliche.” We moved down to Christmas lit up bar and then next to the tennis and racquetball club. I told him I am not a PDA person and he said he understood. He doesn’t have the full lips I lam use to but the kiss was still very nice. I got a text later that night stating he got butterflies from the kiss.
Why is he Mr. Game Changer because I usually go out with really artsy or really math type men, who don’t really know how to romance or just turn out to be jerks. I never thought I could just find a nice guy or a guy who I don’t want to change. It’s a nice change.
Dating and Dior is perplexed!!!
Dec 14th




For the first time ever I am perplexed by my dating situation. I finally met a guy (I have written about our date but haven’t posted it yet) who I see real potential with. The type of guy that makes you feel beautiful without saying a single word. The type of guy I actually trust what he tells me and don’t feel the need to google search. They type of guy who actually listens to everything I have to say and will contact me daily just to see how my day went. He actually text just to see how my papers are going. We can talk about sports, celebrities, and politics and things that are interesting us. He will say brilliant things and I don’t feel intimidated (my vocabulary is growing.) Sex is a subject easily talked about with no pressure. Since living and dating in Boston this is the first time I have met this guy. Someone who is generally nice.
My classmates and friends have read his profile and all stated this is the type of guy I should be dating. So, why am I perplexed? Because I know if this goes sour it will all be on me and my inability to deal with nice guys. I am a real jerk magnet. Guys who offer nothing but challenges to get them to truly see my value. Guys who are wrong and I know I can make right. Guys who are looking for one night stands or the novelty of dating a black chick. Guys who call two weeks later and I immediately switch my mind to think they really do like me. I guess I thought something was always broken about me so I would look at a guys resume and saw the glue they had to fix me, and I gave great weight to that glue that I ignored essentially they were just wrong.
He doesn’t want to change me or fix me. I don’t want to change or fix him. The elements he adds go way beyond the surface of what I thought I was looking for. Unfortunately, on our second date I had it in my mind to find his holes so that I knew our first date could not be that perfect. He gave me nothing to poke at or scrutinize. It took five minutes before I realized why would I set up a failure like this. Just enjoy yourself. I enjoyed myself and he said the perfect thing to me when discussing my school schedule for next semester.
Me: I am taking 6 classes next semester so I am going to be stressed
Him: That’s alright. That’s what I am her for.
Me: You don’t understand you caught me in finals the stress level has been extremely high. it will probably be worse next semester.
Him: No, that’s what I am here for.
There was no sexual inclination, but just straight to the point. His spell was cast in those 30 seconds.
How do I allow myself to handle just a nice guy. Sometimes I feel the drama queen in me wants to come out to rise a different emotion and he can see I am probably not the greatest catch. This is not because I am, but because this is what the dating world has taught me or I have taught myself. Honestly, I can also be the jerk. My sister reminds me the book He Is Just Not That Into You, I am the He.
I also have a habit of falling hard and fast and then moving on to fall hard and fast again. I made sure I take it slow with him to avoid this pattern.
I am scared to put my eggs in one basket because it could fail (again my fault if it does) but I honestly don’t want to spend my date nights with anyone else. The perplexity does not seem all that great but for me it truly feels weird to not be that cynical dating girl but just to be myself and happy.
I guess the true question is: How do I not f**k this up?
Date with Mr. Piano Man
Oct 10th


I will say I had planned for the date to go one way and it ended up in a different direction.
Of course I met the Piano Man online. He contacted me and let me “You are a pretty one”, and I looked at his picture and thought he had a great smile. He is 1/2 Italian and born in Italy so immediately I was hooked. (Have I told you I was Italian in my past life time.) He is an accomplished piano player, who moved to Boston a couple of years ago to work on his masters and attended a very prestigious music school in New York. The next day he contacted me to say he really wanted to go out, but he also warned me he is extremely busy with his studies and a broke student. This is just code for I can’t offer much of anything, and I don’t want to be a boyfriend. I am not looking for a boyfriend I am just looking for dates. (I do have a weakness for the starving artist type.)
We made plans to go out Saturday evening and I asked what his budget for dinner was. He said he can spend $20, I gently asked him if that was for both of us, he replied with $30 for two people. (I honestly have a thing for a man paying for the first date. It’s just how it should be.) I knew my favorite Vietnamese restaurant in Chinatown would be perfect for this date, Pho Pasteur. It’s cheap with large portions.
On Saturday afternoon, on the way to the hair salon for my bi-annual haircut, I received a text message from him saying he wanted to cancel because he thought we were looking for two different things. (Which means he could tell I wasn’t willing to have sex on the first date or be a side chick.) I responded simply OK. I was disappointed and took it to mean he found someone or something better to do. After my hair was done, and I felt cuter than America’s Next Top Model, I sent a simple text saying we should meet. He agreed and the date was back on. Everyone commented that he was a loser and I should not even contact him because I deserve better. I agreed I deserve better, and I am a hot catch.
The plan was simple, I just needed to show him how hot I actually am (my photos do not do me justice) and eat at a really cute date restaurant. As I explained to my sister, he was low on the totem pole and he didn’t have a chance at all. She agreed, I looked hot with the new hairstyle. I know it’s a stupid game, but I was not in the mood to be treated that way. I channeled my best Sandra at the end of Grease, put on my “tell me about it stud” tight black pants, low cut top and leather jacket. I blasted Gold Dust Woman by Fleetwood Mac as I got ready and got into my damage will be done routine.
I headed to Chinatown listening to Rick Ross on the ipod because I knew I was going to have fun tonight. After 10 minutes of him being lost we finally met. He was cuter than his pics and skinnier than I normally like. He had two things going for him, big brown eyes with long eyelashes and super thick lips, my kryptonite.
We ordered at the restaurant and talked about everything from piano hands (apparently length does not matter, but flexibility does.) He taught me some Russian and Turkish words. I even saw pictures of his family. He said “I saw you and thought wow this woman is waiting for me. She is gorgeous.” As George Bush would say “Mission Accomplished.” I could have ended the date there, but for the first time I realized I was doing something I haven’t done on a date in a while, and no alcohol was involved, I was laughing. I mean laughing a lot. Wait, we were laughing. I could make fun of him and he got it. My smile kept going.
After dinner we walked for a long time. I mean we walked from Chinatown to the North End. We finally sat down and talked for 15 minutes. We were very honest with what we were looking for and how we felt about each other I mean brutally honest.
Piano Man: I really like you, but I get a feeling you don’t like me.
Me: Actually I think you are very cute (kryptonite lips)
Piano Man: Really (grabs my hair)
Me: Honestly, I am a cold-fish on first dates. I have a little wall because I am trying to get to know you before I let you into my comfort zone.
Piano Man: I understand that.
Me: It wasn’t my plan to like you, but I do
Piano Man: I want to go on another date with you, and I want to do whatever you want to do.
He mentioned earlier in the date going on a second date, but that wasn’t my plan so I pushed it to the side. When he said it this time I realized my feelings truly changed. I wanted to try to be the best asshole possible, break a heart, and move on, but this did not happen. I actually responded with a “Kiss me. Just one kiss and no tongue.” (I am such a prude on the east coast.) He smiled one peck “Now I want one more kiss.” He obliged. With that we walked to the T and waited. More bantering back and forth and when the C line came, he said bye and I grabbed him real fast and got one more kiss in. (Kryptonite.)
I got a text message later that night stating what an awesome girl I am and how he couldn’t wait to see me again. To the dismay of my best Grease Sandra and Gold Dust Woman, I look forward to seeing him again too.
Funny and available
Aug 26th
I would be lying if I said I haven’t met these types. Ladies, let me introduce you to the Boston dating pool.
Casting a wider net: Overcoming the dating hump.
Aug 23rd
I got a lot of feedback on my dating situation. Apparently, I am not a piranha I just need to cast a wider net. I got advice from 2 friends while on vacation in California who have been very successful in the dating online community
Miz Green: Did you wink at 20 people
Me: 20 people. No.
Miz Green: You need to wink at a lot of people. What is your age range?
Me: 29-39
Miz Green: How old are you?
Me: 31
Miz Green: You need to lower that go to 27. I was out of my current BFs age range, and I am the one who winked at him.
Later, I went to another friends house who also successfully met her boyfriend on a dating website.
Miz Sidecar: Let’s see who is in Boston for you. (She went on blackpeoplemeet.com to see who is available.) Height requirement?
Me: 5’11″ and above
Miz Sidecar: Are you 5’10?
Me: No 5’7″
Miz Sidecar: Age?
Me: 29-39
Miz Sidecar: okay lets look. (we searched through the results of 10 people fitting my description) I think you need to change your age and height requirement and you will be fine. You can go shorter.
The challenge has been set for this month. Be more inclusive in my options. Younger and shorter. (Shorter does scare me because I find guys lie about their height online.) I must:
- wink to at least 20 guys
- go younger
- go with 5’8 and build from there
Help!!!! I lost my Mojo or it got stolen, I think.
Aug 21st
While I was on a good run in the dating arena, ever sense my last date with Mr. Cat Caller my streak has ended or I stopped putting out the vibe, or I stopped caring, or guys stopped caring, or I just need to change my hair to what Jada Pinkett-Smith’s looks like in Hawthorne (it is a great cut.) I will admit I think my ego was bruised a lot more than I thought it would be by that experience. While I can discuss being left in a restaurant and joke about it openly, it actually still sucks.
Honestly, I don’t know what it is. (I like my current haircut, anyway.) I rarely go on match.com, and the people who do email me I am never excited about. I still go out, I still study in coffee shops, I still go to my spinning classes, my arms are swinging as taught by the flirting teacher. Life continues as normal except I feel like a piranha or a leper. The summer well has dried up completely and turned into a Saharan desert with no sight of water within 10,000 miles.
A couple of weeks ago I went to the Martha’s Vineyard and had a female pow wow moment, one of the ladies mentioned exactly ow I felt. “Dating in Boston, you mean the city where guys make you feel like the ugliest person in the world.” Everytime I describe that to another single female of color in Boston, they completely agree with the statement. These are all very attractive smart and funny women, and many of them with advanced degrees and great careers, and passports filled up with destinations they have visited.
Boston is an intellectual town so you would think this is what guys are looking for. Maybe not. The point is this dry spell needs to end soon, and I mean very very soon.
Any suggestions? What is wrong with me? What is wrong with them? Where do I go?
Help!
Flirt! Flirt! Tease. Flirt! My Lesson on Flirting
Jul 26th
No dates were scheduled last week, but that doesn’t mean my adventure stopped. On Wednesday I was invited to a flirting class for Friday night. I must admit I didn’t know if I should be insulted or flattered. I questioned if I needed help in the flirting arena. I actually thought about it until Friday, and I asked around and everyone stated I have this website so why wouldn’t I go. I also remember some of my flirting techniques and realize I am the witty flirt a.k.a. asshole flirt. My method tends to be find one thing on a guy and make fun of him for two minutes, and if he can keep up than we are good to go, and if he can’t, I got to move on. I was told this is “too strong” of an approach, but my response has always been if he doesn’t like it then we won’t work because I am much nicer compared to the dunes my family throws out there. Next thing you know I am signing up. Then I found out the class was sold out and I was put on the wait list. Let me tell you, the wait list is always a great marketing trick for me because then I have to find out what exactly I am being denied from so, I contact the instructor and 10 minutes later I am in.
I arrive for the class and was surprised by what I saw. The men were attractive, and the women were pretty. The people who you least expect to be in a relationship were in one and the gorgeous ones were not. Basically, this is not a class full of fuglies.
The instructor has her PH.d in biochemistry and proceeded to tell us a story of how she was a successful woman in her early 30s with a disastrous love life. She went on to figure out the brain component of flirting, but soon realized it the action also involved the body, and then the soul. Apparently there are four levels to it:
- conscious
- unconscious
- body
- soul
At this point it all makes sense. On a daily basis we do and feel things that run through all four sectors. Did you know 90% of the body is run by the unconscious. (I was a humanities major and a seeker, so this is the only fact I got for you. )I get it. Then we get to our definitions.
Flirting: strategy for letting someone know that you maybe interested in a sexual relationship (body sharing). It feels like positive energy that leads you towards someone else.
Seduction: offering something that you have no intention on delivering or teasing. It feels like a knot in your stomach and you feel like a sleaze.
OK. According to these definitions I am one of the biggest sleaze around. I believe flirtation has sexual undertones, but it does not always have to do with sexual relationships. I have flirted with people at work, married people, women, bartenders, guys on the train, but I am not interested in a sexual relationship in about 90% of them. My body sharing ain’t that easy.
While I disagreed with her on the definitions I agreed on a lot of the other things.
- Change your attitude and find people interesting. I think by opening yourself up to others instead of being judgemental you will get a lot more interesting stories.
- Have energy when you flirt. if you don’t think it will be a good night stay home because your energy is already negative. Positive energy welcomes people to make conversation with you.
- What is sexy? Walking around connected with your body. Being comfortable with your body. Confidence.
I completely agree with point three. I mean how many times have you seen someone you thought they may not be the best looking person, but they are always on dates or getting numbers. This person is really comfortable with who they are on a daily basis, and confidence is always shines through. For this segment of the class the instructor had us walk around the tiny room and told us what are bodies look like when we walk. She was right on with everyone else so I am assuming she is right on with me. I had to walk in front of her 4 times. First she commented on my arms looking stiff. “You have great height and long beautiful arms, swing them.” Then we moved over to my face. “You have a great chin. You have beautiful eyes, and great hair. Hold your chin up higher.” I thought I walked with my chin up but apparently not. I did what she told me and the class clapped enthusiastically, it made the world of difference. I have no clue what I did, but I now remember to walk with my chin up and my arms swinging. For others in the class men began to walk like models and it was very sexy. Women were told to stop hunching over and walk like women and if you didn’t have hips start swinging your waist around to create a confident motion. I found this part of class the most helpful.
Flirting starts with feeling and being sexy, The next step is to give your interests compliments. I feel compliments should be earned not just said because it is Tuesday, but I am single so I need to give compliments.
Next:
- Match their movements. If they shift you should shift also. Not complete mimicry, but just copying some
- Body alignment. When standing stay centered with them to keep focus and to add flirtation shift slightly out of the center or cock your head. Also slight touches to the shoulder and arms. (I hate being touched if I don’t know you, so my response is no.)
- Copy communication styles. If they are using visual, auditory, or kinesthetic words. you should respond in the same manner to increase connection
- Ask for what you want so everyone is on the same page. Allude to being asked out if that’s what you want ladies.
Finally, understand REJECTION will happen. She then taught us a self hugging tapping the arm thing to help get rid of the sinking feeling or tension in the shoulders that occur when your body responds to rejection. After three minutes the movement actually worked. A feeling of sadness came over the room as people realized they still have to go out and practice these techniques and know rejection is imminent. We had to tap ourselves for 3 more minutes.
The class ended and everyone rushed out the door. This week I will try out these new methods in talking with men. Positive attitude.
Be aware

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