Thank you for reaching out about the site. It helps to know what's working (and not working). As I mentioned yesterday, your questions -- and your regular Love Letters entries -- can be sent to my email at meregoldstein at gmail dot com. And you can always find Love Letters under Short Cuts within the Sections menu (top left on the Boston.com homepage).
I have to postpone chat until next week because I am visiting a high school today to talk about Love Letters. I'll let you know what they think of it.
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
A: Usually I'm all about conversations and clarity, but in this case I'm not so sure that a talk will get you anywhere. What's the best case scenario here? That he admits that he had a crush on you and then ... he continues living in Texas? He's far away, and it's not like he's doing much to bridge the distance. You need someone nearby who doesn't have to be coaxed. Moving on would be a good thing.
Of course, if you're freaking out about what happened and know that you won't be able to move on, you can ask him how he feels about you. As in, "Was there romantic potential in Texas? Why didn't anything happen? Can we start something now?" You have to be that clear. You can’t just "continue pushing." You've dropped enough hints to bring him out of his shell. As you learned in Texas, hints usually aren't good enough.
Readers? Should she let this go? If not, what should she say to him? Any potential here?