[NYCgirl]

I’ve got a unique situation. I met a man at work several years ago and we became friends. However, because of the project-related work we do, we would go through periods of seeing each other daily for months, then moving on to new projects, then working together again months later. In between we had little to no contact as we were in opposite cities. Over time I developed a crush on him, but would never have acted on it — I don’t believe in dating colleagues, and was in a long-term relationship. After I left the company, I reconnected with this man with the hope that we could develop a close social relationship. (I am now single and we happen to live in the same area.) I’d classify our former relationship as somewhere closer to friends than acquaintances, but because we’ve always had a sporadic contact pattern I never felt like he was the sort of person who I could call in the middle of the night. I figured that at a minimum he could become a friend I’d see on an ongoing, regular basis — and best case scenario it would turn romantic. (We had a couple of semi-flirty late nights at work in the past so it didn’t seem completely out of the question.)

We met for dinner and had an amazing time. In fact, I left wondering whether it was a date vs. two former colleagues catching up. He didn’t know I was single until that day, and he almost immediately asked whether he could join me the following month for an activity in my neighborhood. Things were a little flirty, and when we parted he pulled me close and didn’t let go for a really long time. Thereafter we had a pretty regular email correspondence (our typical method, since we’re often in very different time zones due to business travel). We made tentative plans to get together again. He went kind of silent. I reached out to confirm plans and he let me know that he was about to start a new project overseas. He suggested we reconnect after his return in six weeks to plan an outing. I decided to wait to see whether he’d reach out.

I didn’t hear anything for several weeks after he should have returned. Rather than just write him off (which I might have done if we had just met and had one date), I thought about how I’d handle the situation with any other friends. I’d certainly reach out to see if they were okay. So I sent a casual note letting him know what was new with me and asking if he’d like to get together again. He responded a couple of weeks later, apologizing for the delayed response because he’d recently had an email program upgrade and my message had been diverted to his spam folder. He said he was once again on his way overseas for the next phase of the project but definitely wanted to see me and would reach out when he returned and had time to get together.

That was in November. I had kind of decided that I’d just sit and wait to see if he reaches out, but last month I decided to send a note asking for clarity. I explained that one of challenges I experienced when we worked together was the fact that all the travel leaves little time for a personal life, so I understand his schedule. But I also let him know that I had hoped to include him in my circle of close friends and am disappointed that we haven’t been able to develop a deeper social relationship. Lastly, I asked whether he would clear up my confusion about this, since I felt like he sincerely wanted to keep in touch and I don’t understand the recent silence.

Crickets. Now, it is possible that the message never made it to him (per his comments about the email system troubles). But even if that’s the case, why wouldn’t he follow through on his promise to reach out to a friend? As I said, I could interpret this as a classic male brush-off if the situation were a dating relationship and he decided he’s just not into me. But that’s not what this is.

I’m a problem solver, so I’ve run over a million scenarios in my head. Could he somehow sense my romantic interest and is uninterested? Is he potentially interested in romance but doesn’t think I am? (I did start to break the post-dinner hug goodbye, which is when he pulled me even tighter and didn’t let go.) Is he simply unable to multi-task and think of people on a different continent than he’s on? Did I blow this by making him feel inadequate through the directness of my last message? Is he a toxic bachelor who is unable to commit to even a mere friend?

What do you think is going on here? Should I simply pick up the phone and risk waking him in the middle of the night in case his email system didn’t deliver the message, or is it better to leave things alone and write him out of my life?

[AskApril Masini]

I think you want him to respond romantically, or at least as a friend, and because he hasn’t, you’re trying to bend the truth. 😕 What’s going on here is very clear, but it’s disappointing, so you’re trying to turn disappointment into confusion. If you’ll just step back a few feet to try and get some perspective, you’ll see that he’s not that into you. 😕 I’m sorry to be blunt, but I think it might help you.

You’ve left out some details about your dinner together, like who initiated the date, did he pick you up or did you meet at the restaurant, did he pay for dinner and did he kiss you goodnight? These are all possibly corny and cheesy details, but they’re also landmarks of a date. When you take these opportunities away from a guy by asking him out, etc., you don’t get to see how interested he is. The bottom line is that if a guy wants to date you, he will. He’ll call you up, invite you to do something, pay for the date and try to impress you, kiss you goodnight and call you for a second date. Old fashioned? Maybe. Effective? Definitely.

Instead of delving into [i]his[/i] head and trying to figure out why he’s flirtatious when you’re together, and gives you radio silence when you’re not, ask yourself why [i]you’re[/i] trying to figure this out instead of accepting those crickets, and then looking around and smiling at all the guys you meet during a day, giving them a chance to ask you out because they might really want to date you!? 😉

I hope that helps.

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[NYCgirl]

Yes, I understand that his not responding is sending a clear message. And I agree that I wish he was into me. I’m not sitting home pining away for him (anymore), and the reason I’m trying to figure this out is that I’m new to the dating game (previous relationship lasted 25 years) and am trying to figure out how to predict a disappearing act in future should I be faced with this again. In this particular situation, I’m also confused about how/why he pulled such a disappearing act with a friend (vs. potential girlfriend) — or whether he put me in the potential girlfriend category and then disappeared.

The details: After I reached out to let him know of my job change and move to his area, he suggested that we meet. We went back and forth for several weeks trying to find a mutually available date. Once we did, he picked the restaurant and we met there (I live an hour outside the city so picking me up wouldn’t have been practical). I looked at it like two old colleagues reconnecting. However, once we sat down and he learned that I am now single, the conversation quickly turned personal — which he initiated. Halfway through dinner I mentioned that I had been doing a lot of wine tasting on weekends, and he asked if he could join me sometime within the next couple of months. We talked about other activities I’ve been doing since I moved to the area, and he expressed interest in some of those as well.

Other than a handshake when we met four years ago, we had never touched — which I always thought was kind of strange since over time with other male colleagues you occasionally nudge each other or high five after a big win. It’s almost like he was afraid to touch me. But after our dinner (he picked up the check), he held the door for me and put his hand on the small of my back to guide me. Once we were on the street he pulled me close in an embrace — extremely close. I didn’t want to be inappropriate (after all, the intent of dinner was as two colleagues catching up) so I started to pull away after a few seconds. He squeezed me tighter and didn’t let go. When we did finally part, he ran his hand down my arm and held my hand for a moment. His last words were that he’d check his schedule to see when he has time for wine tasting.

As I said, we were in regular email contact for several weeks, then he went overseas. He’s always kind of been an out of sight, out of mind, kind of guy in between our joint projects, so I didn’t think too much of it. There was some sporadic contact after he returned, but it has tapered off to silence. Why I’m so confused is because I feel like I definitely got “buyer” signals at dinner, and didn’t rule out the likelihood of getting together again (we even made plans on a couple of occasions that had to be diverted due to these overseas trips). Is there anything in this story that I should have seen over dinner which would have prevented me from getting my hopes up afterward?

[AskApril Masini]

[quote]Is there anything in this story that I should have seen over dinner which would have prevented me from getting my hopes up afterward?[/quote]

No — it sounds like you had a nice dinner together. But he never called for a second date. There are lots of reasons guys don’t ask you out again — many have to do with you and many have nothing to do with you. He could have been playing the field and met someone he liked better. He could have gotten busy with something you know nothing about, like a sick relative or just been very busy with work. Or he could just not have been interested in a second date. Rather than second guess yourself and him, my advice is to let it go and move on.

I appreciate your being new to the dating game after 25 years. Things have changed — that’s for sure. 😉 One of the biggest changes is that it’s a lot easier to date, so you should assume that anyone you’re dating is also dating other people — especially during the first few months. We all have very busy and connected lives thanks to technology and reading the signs of a date have gotten to be a lot more black and white to prevent confusion. If he asks you out for a second date, the first date was the reason. If he didn’t ask you out for a second date, you should move on and not worry about it. If, however, you find you have a string of first dates that never lead to second dates, then — and only then, should you consider it’s something you’re doing. But if one date didn’t lead to a second, don’t worry. Next! 🙂

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[NYCgirl]

Thank you, April. I’ve been turning this over and over in my mind for many weeks trying to figure out what I could have done differently. I feel better knowing that it isn’t necessarily my fault.

[AskApril Masini]

It’s not your fault. 🙂

Next!

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