Option 1, 2, or 3?

[SapphireSlippers]

I was out processing a guy at work for early retirement (he's 50). There's an interview that takes about 30 minutes, and it took us about 90 because we were laughing so hard and talking and enjoying ourselves so much. There was that rare spark and I saw his eyes light up when I laughed.

 

He's going to start a second career consulting in the middle east on 90 day stints a couple times a year. And the day after our interview, he had minor throat surgery for sleep apnea.

 

About a week after his surgery, I sent an email giving him a lead about consulting I'd promised him and said I hoped his surgery went well.

 

He wrote back a long email that was fun and personal and we started up an email correspondence. It was a mixture of work, joking, and a few lighthearted personal revelations.

 

About the 3rd email, he said thanks for my help and he owed me a drink. I said I could use a drink and mentioned something at work. Maybe that was cryptic. Anyway, he said nothing more of it, and the emails vered more towards shorter and more work related.

 

Then I said something really funny and something complementary, and he wrote a long personal 5 paragraph email, talking about himself, some of his bitterness at a work situation and about what he's hoping for in the future, plus a couple complements for me and several jokes. At the end he said, thanks for looking out for me, like I said I owe you a drink. (he sent this twice in one minute). This was 20 days after the first mention of a drink.

 

Thinking I was cryptic the last time, I responded to his email and at the end said, 'if you're serious about the drink' I'll take you up on it.

 

Didn't hear anything, but two days later, he had to go to a retirement seminar in another part of the building. I'd gotten him an advantageous time slot and my boss is an old friend of his, so he suddenly appeared at my desk. There was no need to, the seminar was on the other side of the building, but I guess he wanted to say hello.

 

Unfortunately I'd just taken a big bite of my sub and had a full mouth and could only smile helplessly. He grinned and went to stand in my boss's office door about 12 feet away. But he was half turned towards me and as he was talking to her he was smiling at me and making eye contact to include me in the conversation.

 

At one point my boss said something that might have embarrassed him (he told her, she looked good. She said, I can't say the same about you, I told Sapphire Slippers just this morning you came to the company a good looking guy, a stud, and now look at you, you look like a junkyard dog. Why'd you let this job do that to you?)

 

At any case, when he left he just smiled and waved and said, "See you."

 

The second mention of the drink was Tuesday. He came by my desk Thursday. Friday he had his offsite retirement party (I didn't go, nor did my boss). I've heard nothing. In the back and forth of emailing, it's his turn to write, and it was my last email where I let him know I'd go out for a drink.

 

What should I do:

 

1. Nothing. If he's interested he'll follow up. (but I notice a lot of guys really seem to need a LOT of encouragement these days). Maybe also I'm just too impatient. Timelines moved faster 25 years ago when I last dated.

 

2. Sunday night send a brief email asking how the party went. See if he wants to resume an email relationship or whatever... If he doesn't answer again, THAT's the answer.

 

3. Wait until after Xmas when he comes in for final outprocessing. At which point I would walk him from the building (required). It's usually my job, but my boss might do it because they are old friend. If I don't get to do it, maybe send an email that evening saying, "Sorry to miss you today..."

 

(He's not shy, and he doesn't have a girlfriend, at least not an official one; no live ins, none known to his wider circle of friends. He might have a friends with benefits, or an understanding with someone he hangs with. He spent the night in the hospital and had no visitors.)

 

Advice?

[dasein]

Was this a layoff type early retirement? one of those "take this offer or else?" My best guess is he doesn't want to maintain a close connection to a company he may have mixed feelings about, and starting up with you might create such a connection, at least in his mind. He may be interested in leaving things in the past and moving on to the next phase of his career cleanly.

[SapphireSlippers]

Nope, just early retirement from the Federal system and moving into a more lucrative private job. He's done 26 years and has two house paid off and his kids out of college, etc... They are offering $350K a year if he works 40 weeks. He wants to work about 20 weeks overseas and pursue his sports/hobby which is also lucrative.

 

He has very close ties with the work place, lots of friends, and has a habit of keeping friends long-term.

 

But if he wanted to walk away, why offer the drink, twice? Or has the dating world changed in the 20 years since I've been in it? It used to be a drink meant within a week or so you went out for a drink. Is it just a male version of 'let's do lunch sometime'?

 

I have to say that since I've reentered the dating scene 3 years ago, men don't seem to be very proactive in dating; they seem to leave it up to the women. I went out Wednesday and he wouldn't choose a day, but accepted what I choose, then it was painful to choose a place. I came up with 3 places I enjoyed and he couldn't commit to one. Then we decided to share an appetizer, and I said, these three interest me and he tentatively said he loved hummus and I said, hummus it is.

 

But it's not just that guy. In the last 2 years since my divorce I've dated 10 guys, and it feels like I have to do all the heavy lifting, but they are eager to go along.

 

Is this an older guy thing? About half of them are high powered guys at the top of their field, go getters.

I'm puzzled by this phenomenon. They are very receptive if I push, and if I don't they drift off. But if I pop up and push again, they snap at the opportunity.

 

But it sounds like your question that you think he's not interested, and maybe it's because he wants to move on... or something else, but ultimately he's not interested, or he would have followed up by now on the drink?

[dasein]

Well I agree with you as to men being not proactive enough in dating today. Don't want to turn this thread into a gender debate and tell you why that is, you can probably figure it out yourself, and like most dating issues, the fault is shared equally or almost equally between the genders.

 

In light of the further info, he sounds like he has interest, but either a) not enough interest to follow through with his flirts for some reason, or b) if he's going to be doing lots of intnl travel, may not want to start something up right now?

 

Also in light of what you post, is there a chance he wants to stabilize the new work scenario before dating? This sounds like someone who is going to call you a month or two down the road, settled into the new thing, and ask "OK, the stack of stuff from the new thing is only 3 ft high on my desk now, about that drink?" Good luck whatever you decide.

[SapphireSlippers]

Could be.

 

When the emails devolved into just work talk and got shorter, I had said everything I had to say about my official involvement with his retirement. So there was no official reason to continue emailing. I ended an email with: Good luck to you in your new endeavor; if you think of it a couple months from now, drop me a line and let me know how everything worked out.

 

That's when I got the last 5 paragraph email with the second mention of the drink.

 

So Option 1, 2, or 3?

[dasein]

If I were in your shoes, 1. He knows where to find you and that you have responded positively to his overtures. Wait for the final interview and if he is still interested, he will likely stop by your desk. Sometimes doing nothing allows you to gain more useful information than any active steps, so sayeth Lao Tzu. In the meantime, certainly wouldn't foreclose other social options.

[FitChick]

I don't know about this guy, but generally successful men who get divorced are used to having their wives make all the decisions about their social lives. They are high powered at work but perhaps want to relax and let someone else take charge afterwards. Also, I think a lot of men are pussy-whipped and afraid to put a foot wrong with women because they are used to walking on eggshells with their exes.

 

I would do nothing in your situation because you don't want to chase him. It's not like he doesn't know where to find you and you were certainly receptive to his invitation.

 

It's also possible he only likes you as a buddy and realizes you are interested in more than that.

[SapphireSlippers]

Well I agree with you as to men being not proactive enough in dating today.

 

So two opinions that men expect women to be more proactive in dating these days (at least older men), which indicates I should send another email of interest.

 

But also two opinions I should do nothing, because he knows where I am.

 

Aren't those contradictory opinions?

 

It's also possible he only likes you as a buddy and realizes you are interested in more than that.

 

But what's the point of mentioning going for a drink twice?

[dasein]

So two opinions that men expect women to be more proactive in dating these days (at least older men), which indicates I should send another email of interest.

 

No, the acknowledgment that men aren't as proactive as they should be today does not mean that more contact is required in your particular case, you have been plenty proactive so far. No need for further contact to signal interest from your end.

[insertnamehere]

You only regret the shots you didn't take.

[SapphireSlippers]

You only regret the shots you didn't take.

 

Well, I was debating last night and I read over all the emails. 18 in 20 days.

 

A couple things struck me.

 

1. The first email I sent was 100% work related and I sent it to his personal email not his work one because he was home on sick leave. He didn't respond for a week and when he did he said, he never checks this one because it's seldom used. In the next 20 days we emailed 18 times, same thread, just hitting reply. He always answered my emails within hours. I thought: if it's seldom used, but he's answering almost instantly (for email), does that mean he's interested enough to watch for my emails?

 

2. I realized that while he shared personal things with me (maybe 2/3 of his emails were personal, 1/3 business related); I was the opposite: I focused mostly on business with a line or two of friendly, humorous, personal. Maybe he was giving mixed messages about the drink, but I was really giving cryptic messages as well. In fact, he always answered within hours, but once I took 3 days to answer and once I took 6 days to answer (over Tgiving weekend).

 

3. In the back and forth it was his turn to reply. But within a day or so of my acceptance of his 2nd drink suggestion, he showed up at my desk when he didn't have to. So maybe that counted as 'his' turn.

 

4. If he wasn't interested, he'd ust not answer or answer politely but distantly. I can live with that. I won't be crushed or devastated, only some disappointed, but no worse off. But if he was interested, I'd be happy and maybe something would come of it.

 

So I wrote an email last night. About 4 words of business and a couple paragraphs personal, including a rather funny story about my 20 year old son. He wrote back less than 90 minutes later, telling me about how 20 years ago yesterday he was almost killed in a shoot out. Then he told me about his retirement party and some other stuff.

 

So I'm very happy I wrote.

 

I'll write back tonight. He gave me a lot to ask about and I'll add some in about me.

[curlygirl40]

 

 

3. Wait until after Xmas when he comes in for final outprocessing. At which point I would walk him from the building (required). It's usually my job, but my boss might do it because they are old friend. If I don't get to do it, maybe send an email that evening saying, "Sorry to miss you today..."

 

 

 

Is it possible that this ^ is what he's waiting for? The final outprocessing? Do you think it's possible that until he's completely out of the job that he wouldn't feel right asking you out for real?

 

I think he's definitely showing interest. I agree with you there. If he's not at all interested would he write 18 e-mails in 20 days just to be nice? Probably not. And some of the ways that you had thought to keep in touch do not seem pushy or needy or 'chasing' him to me. If you feel like you've established somewhat of a beginning of a friendship then why wouldn't you shoot a quick e-mail asking how his weekend was, or how the new job was going, or whatever?

 

I know some people avoid starting something new at the holidays because they are busy and they also want to avoid that 'do I get them something for Christmas, do I invite them to the work holiday party', etc.

 

Keep on him without making yourself too obvious. lol That's my advice. Have fun!

[SapphireSlippers]

I think you may be right.

 

Tonight I sent two emails and he sent three. We veered back though to mostly work related stuff (gossip).

 

Talking about his disgust at the top boss's sleeping around he said he may have screwed up at times in his career, but he never laid a hand on a female employee, ever (although I know he's been divorced 11 or 12 years). He finds boss's behavior despicable. So he seems to have had a policy of no work romances.

 

Ok, at the risk of making the males on this forum groan and say: don't over analyze, I noticed this: He signs his emails differently each time. (his name's not Tom).

 

1. Tom ( instead of Thomas)

2. Tom Lastname , personal phone #

3. Tom Lastname , personal phone #

4. Tom Lastname , personal phone #

5. Tom

6. Tom Lastname , personal phone #

7. Tom

8. T

9. Tom Lastname , personal phone #

10. no name at all

11. Tom Lastname , personal phone #

12. Tom Lastname , personal phone #

 

The last two emails he sent within 15 minutes, without me answering between. These emails are all on one thread, and he must be typing his signature each time since it's different. Since he keeps typing in his phone number, does that mean he's hoping I'll suggest calling? He doesn't need to keep typing it since I can scroll down a couple inches and find it. He also doesn't need to keep typing his last name, I know it. So it's probably meaningless.

 

Gosh I'm so out of practice with this stuff. Somehow it seems so much easier when I was 22. But I read the questions of the younger posters here and suspect I just might not remember.

[insertnamehere]

You should call him to explain to him how to setup a default signature at the end of his emails!!

 

Jeez . . .

 

No, it's not a signal. It's just basic business writing to sign off with contact info. I do it almost as a reflex.