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I've taken a break from dating for some time now, and have just decided that getting involved again would not be the worst thing in the world. Some background....I'm an attractive 40 something female who looks ten years younger. That's part of my issue maybe. I am looking for men in their fifties, and they think I'm 32 I think.
Anyway, already I have two situations going on that I'm curious about. They both involve men at my workplace. I usually would keep romance away from work, but I'm only on contract and won't be there forever. Both of these men are past fifty, single, professionals.
Guy #1--- We talked in the break room several times. One day somehow we locked eyes for several seconds. The next day he came up behind me, said good morning, and when I turned around had the biggest grin on his face. I realized that I had never seen him smile. I said good morning, and continued on to my desk. Later in the week, we had another conversation that just didn't seem as natural as our previous ones, but he was still making eye contact and smiling. That was on a Friday.
The next week he was very obviously avoiding me, as in, he sees me coming and goes the other way. He did this for a week, was out of town for a week after that. Today he has come back and is back to sayi9ng 'good morning' and smiling and saying hi.
My best guess is that he was too nervous to interact with me, and now something has changed that.
Guy #2--- He let me know he was interested in me a couple of weeks ago. He acted nervous around me after that, but calmed down after a few days. After a week, I said something that let him know I was interested also. He gave me a big smile, looked into my eyes, and BLUSHED. I didn't see him for a few days after that.
As of today, he is not responding to me in the same way. I get the definite idea that he is not that into the idea of taking up with me as he had been. He is still making good eye contact though, and I think that if he had decided he was no longer interested that he would not be doing that.
My idea is that when he realized that he could actually be with me, he backed off a bit and is wondering if that is really what he wants.
I am a one guy girl, and I know even if I weren't that I could only date one guy from work within a reasonable amount of time. I am attracted to both of these men, and like them both. I'm curious as to whether either of them will 'man up' at some point and attempt to proceed. Any advice or insights?
Could it be that they really do want to avoid a work place relationship?
I am not sure. There is a girl in my office, and she and I had talked, briefly, introducing ourselves last year and talking. Good banter, not a bad looking woman, but I don't date at work. That is a nono rule for me.
She has made some outward gestures to let me know she is still interested, of course I am with someone now and wouldn't betray that trust unless she was coming home to see both of us.
I think I would walk up to, whichever guy you like best, and just say, "Hey John, so are you ever going to take me out for a drink or what?"
He'll appreciate it, or you'll scare him off. If you scare him off, I don't think you'd want him anyway.
Ever think about finding a late 30's guy? My suggestion if you haven't dated in a while, get out, play the field a little.
How long does your contract last? It could be that they're not "manning up" because they have to observe behavior guidelines in the workplace. There may be a no-socializing/dating rule. They may be skittish about potential harassment issues.
How old is Guy #2? Are you only interested in older men, or are guys in their 40's ok, too? haha, he blushed! Cute. All of this sounds a bit highschool, but given the realities of the workplace today, it's probably par for the course, though Guy 1's avoidance thing sounds weird.
Find out what the rules are for that office regarding fraternizing. Your best (and possibly only) bet will be to wait until your contract is almost up, and then have lunch with each guy, or whichever one you prefer (I'm voting for Guy 2, for now), explain that you're leaving soon but would like to stay in touch, and see what they say.
I think I would walk up to, whichever guy you like best, and just say, "Hey John, so are you ever going to take me out for a drink or what?"
Almost this exact line was used on me recently at work:
"So when are we going out to dinner?"
I simply said, "Whenever you're available!"
She later confessed that she "didn't think she had a shot until (I) said yes", at which point she knew it was game on. I guess she didn't know how much value I put on initiative
Guy #2 is, um, my boss, and I think he is in his late 50's. My contract will last 1-7 months longer. Kind of up in the air. The company I work for has no rules about dating that I know of. There is a couple who both work in my same department.
Guy #1 works in a different department, but on the same floor, so I see him often but do not work with him.
The boss thing would be a sticking point, if I were a permanent employee. I do like him a bit better, and would be willing to wait until my contract was up to date him. Or, we could be discreet for a few months. But I just wonder why he has been going out of his way to indicate his interest if he was not planning on pursuing it? He was trying to warm up to me for a few weeks at least, and I noticed, but was not certain because he was being too subtle at first.
Oh, and I'm not against the idea of guys in other age groups. But men my own age and younger are often interested in having children, and I'm past that point. It seems to be easier to find dateable men who are a little older, even though I have to weed through them a bit more to find someone who is still active and reasonably attractive.
Guy #2 is, um, my boss, and I think he is in his late 50's. My contract will last 1-7 months longer. Kind of up in the air. The company I work for has no rules about dating that I know of. There is a couple who both work in my same department.
Guy #1 works in a different department, but on the same floor, so I see him often but do not work with him.
The boss thing would be a sticking point, if I were a permanent employee. I do like him a bit better, and would be willing to wait until my contract was up to date him. Or, we could be discreet for a few months. But I just wonder why he has been going out of his way to indicate his interest if he was not planning on pursuing it? He was trying to warm up to me for a few weeks at least, and I noticed, but was not certain because he was being too subtle at first.
Regarding your boss...
It is my understanding at most companies supervisors cannot date their employees. And if it happens, one of you or both of you could very well get into serious trouble... possibly fired. So even if you want to discretely date for a few months, I would find out if what the company policy is first.
It might be better to wait until after your contract ends.
Is your boss married? That is an important thing to find out before considering dating him.
Now that we know Guy 2 is your boss, his behavior makes perfect sense. He had to back off a bit, but he's still interested. Since Guy 1 is in a different dept., why not ask him to join you for lunch? If nothing long-term works out there, you can invite him to drinks as a farewell gesture, and see where it goes from there.
And just fyi, there are guys in their 40's out there who aren't into having kids, and they're looking for women like you. Sure it takes more weeding to find them, but IMO it would be worth it, to have the prospect of being with someone who can be as active as you, and share a longer life with you. Late 50's is almost 60. Just something to consider.
edit: Good point made above; have you checked to see if either of these guys is wearing a ring?
Wait until your contract ends and ask both out on your last day - on separate dates of course.
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All of this sounds a bit highschool, but given the realities of the workplace today, it's probably par for the course, though Guy 1's avoidance thing sounds weird.
