Love Letters, Boston.com, 16 April 2014:
Hi Meredith, I’m a consultant who travels for work and I live in Boston. In September I met a guy while working as a contractor at his company in Texas. At first it was completely professional, but as we worked together it became obvious that we shared some common interests. He’s very shy and seems a bit unsure of himself and is also two years out of a divorce from a long marriage. I’m very shy as well, so there were about two months of smiles and giggles or stares across a conference room table. I started breaking the work-only barrier with a text. He responded and our non-work relationship started growing to the point that we exchanged fun texts and e-mails and became more relaxed with in person conversation. At the beginning of 2014 I got frustrated with the slow progress and with the knowledge that my contract was coming to an end. I encouraged him to plan a fun activity for us after work — he planned drinks out with some coworkers, a couple of his friends and me. It was a fun night and he paid for my drinks. The night ended with a hug from him. We had drinks again the next night with some coworkers and some of his friends. He seemed to be getting more comfortable with opening up to me by sharing more info about himself in the days/weeks that followed. We also made plans to take a day trip to an air show (we have a shared interest in aviation).Things seemed to be progressing as we got more comfortable with each other. The week before the air show some things changed at work and it appeared I’d be leaving his company sooner than thought. He started to pull back and be more distant with me. He also suggested we cancel the air show day because the planes that would be there weren’t worth the drive. So we cancelled and I was a bit hurt by that, which he knew. We had drinks the Thursday before and he begged me to do something else with him that same day that we had the air show trip plan. I was too smitten to decline and agreed. That day, after I contacted him to confirm plans, he cancelled saying he wasn’t feeling up to it. I was of course quite hurt and upset and kept it professional at work but made sure he knew, and he made an effort to get me to talk to him again and win himself back into my good graces. We had drinks a few times after that, usually at my suggestion. And we’ve continued to share texts and emails back and forth. I’ve since finished up my work with his company. On my last day he was visibly sad I was leaving but didn’t say anything. We left sharing a hug and agreed to stay in touch, but have really only shared a few texts over the last month, all of which have been initiated by me (but he always responds — usually immediately). We also never discussed the flirting/connection between us. Since I left, I’ve thought about him every morning and every night before I go to sleep. I’m completely head over heels for him (very unusual for me) and I feel like I at least want to have that conversation. But the little voice in the back of my head says if he wanted something he would find the courage to get over his shyness/caution and stay in touch with me. A male friend agrees and has advised that I should just move on, and a female friend feels like he is just trying to forget what we shared and has encouraged me to keep pushing to stay in touch. I’m exhausted trying to encourage him through his shyness/post-divorce caution, but I want a firm answer and maybe something more than just friendship from him. Or I’d at least like to know that he wants more too and so that we can have that discussion to determine if it’s a possibility. Is his lack of initiation in communication with me my answer and I need to just move on? Or should I follow my heart and continue pushing? And how do I go about asking for that conversation at this distance? – Love Sick Consultant, Boston
Dear Love Sick Consultant,
The Bad Advisor opened her computer and turned it on, then waited while it connected to her wifi. Then she opened Google Chrome and checked her email and played some Doge 2048. By this time, she was thinking about reading some advice columns, so she opened her bookmarks tab and began reading advice columns. Eventually she got to your letter, but not before she grabbed a cup of coffee and emptied the cat box, because the cat box was dirty. She then began to read your letter.
As she was reading your letter, the Bad Advisor’s eyes looked at the screen which had letters on it, and together the letters made words which also went together in order to make sentences. These were sentences that you, letter writer, had written. They told the story of you and your star-cros’d beau, whom you once encouraged to plan a “fun activity” for you and who did indeed plan a fun activity for you. That activity was going to a bar with your coworkers. It was fun, and your beau paid for your drinks and gave you a hug.
The Bad Advisor stopped reading your letter for a second because she needed to refill her coffee and also stand in front of the refrigerator, which had some cheese in it. Should the Bad Advisor eat cheese? Or should she wait and eat cheese later? The Bad Advisor ultimately ate no cheese. Should she have eaten the cheese? The cheese was definitely in the refrigerator and definitely could have been eaten, but it wasn’t eaten by the Bad Advisor. Looking back, it is hard to say whether the cheese should have been eaten or not.
Then, with more coffee in her mug because she had refilled her coffee mug, the Bad Advisor continued to read your letter. Then things got really interesting, because things progressed when you spent more time together. You spent time together by hanging out together and getting drinks. Your coworkers also were there. Sometimes though your coworkers were not there, but neither was he, like that time that you made plans on a Saturday. The plans were going to be going to a plane show together, but you did not end up doing those plans. You did not end up doing those plans because your beau thought some of the planes were boring but he also pulled back and became distant from you because your contract was about to be up at work. The contract, which was about to be up, was about to be up sooner than you thought it would originally though. That made the Bad Advisor feel sad for you, because you were also sad when your contract was going to be up before you thought it was originally going to be up, and you hadn’t yet had a chance to go see the airplanes with your beau, who wanted to do something besides go see the airplanes except when he invited you to do something that wasn’t going to see the airplanes he didn’t go do the thing that wasn’t seeing the airplanes with you.
However, the Bad Advisor continued to read your letter and was pleased to find that even though you didn’t get to go see the airplanes with your beau and you also didn’t get to go do the thing that wasn’t seeing airplanes with your beau, you did get some drinks with him. You also exchanged text messages and you exchanged emails also. But then your contract was up—sooner than you thought? this is unclear—and he was sad but he hugged you.
Then, the Bad Advisor read the last part of your letter where you talk about how you exchange text messages to which he responds and you think about him in the morning times and in the night times, because flirting/connection. The Bad Advisor then learned that you had asked your friends for advice, one of whom is a male friend and the other of whom is a female friend. They did not give you the same advice. In fact, the advice your friends gave you was different. One of your friends, the male friend, thought that if your beau did not say something about your flirting/connection in the seven months he had a chance to do it in front of your face while you lived in his state, which is Texas, he probably did not want to do it. Your other friend, though, who is a female friend, thinks that your beau wants to forget you forever and so you should push him to stay in touch with you because he wants to forget you.
The Bad Advisor was nearly finished reading your letter at this point, because it was getting to be near the end of the letter that you had written about the man you worked with in Texas but you live in Boston with whom you had a flirting/connection. This is the part of the letter where you asked for the advice that you wanted about whether you should continue pushing for a relationship with a man who had months and months to ask you out on the date that you never told him you wanted to go on with him but who never asked you out on the date that you never told him you wanted to go on with him and with whom you never vocalized any romantic interest but in whom you had a lot of romantic interest but no matter how many fun emails you sent him and no matter how many fun activities you suggested he plan he never understood the romantic interest you never expressed to him, despite flirting/connection. Now you would like to know if you should ask for a conversation about talking about your flirting/connection even though he is a shy divorced person who never stopped being shy even though you wanted him to stop being shy a lot. He is shy, though. Maybe he needs many more months of being encouraged to plan fun activities before he can be not shy with you.
The Bad Advisor finished your letter and thought about it for a while. By this time, she considered the fact that your beau is shy but she also considered the fact that you want him to be not shy, and she also thought about the fact that being shy is probably the reason your beau had months upon months of time in which to express the vaguest sense of romantic interest but in which time he didn’t do that, so he probably loves you with the burning fire of two or three suns, maybe five or six suns, depending on how hot the suns are, but he is shy so he didn’t say anything about it.
In response to the question you asked in your advice column letter, in which you seek advice about whether to follow your heart and continue pushing, the Bad Advisor had some thoughts. She concluded that you should follow your heart, and also that you should continue pushing.