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I have been co-workers with this guy for a little bit over a year but didn’t get to see him often except when we both showed up at company parties.

He seemed to be interested in me. First approached me to start a conversation at one party and then asked me out for a drink at the end of another company get-together. But somehow it felt a bit like a booty call, and I wasn’t in the right place to start anything, so I didn’t take him up on it that time.

After radio silence for almost half a year, he connected me on LinkedIn while I just started a process of leaving this company. He might’ve heard of something. But after we connected, he never texted or interacted with me in any ways.

It’s been another six months, and I’ve been busy with job searches and a lot of stuff in life. Now that things have settled a bit, I would like to at least have a coffee with him and see if there are still possibilities. I’m not sure whether he’s looking for the same thing, but at least I don’t want to have regrets for any longer. Things that recently happened in my life have changed my perspectives and I don’t want to wait for the perfect moment for things to happen any more.

The problem is I don’t really text guys first, ever. But outside of LinkedIn, we don’t really have any other means of contact. So it’s not possible to just “bump into” him. I’m thinking about text him like:

Hey, long time no see. Thanks for connecting with me. How are you?

And see how things go.

How can I get back in touch with a soon-to-be ex-colleague that I'm interested in when the only way I have of contacting him is via LinkedIn? I'd like to make him aware that this is not a casual thing but a friendly coffee to get to know each other.

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  • Are you two still at the same company? – XtremeBaumer Apr 4 '19 at 12:57
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    What is wrong with the way you are thinking of contacting him? What are you afraid will happen? Are you afraid by the fact that he might just ignore you? Or that he might misinterpret your intentions? – Ælis Apr 4 '19 at 13:04
  • @Ælis I don’t want things to be awkward, since it’s been a long time - I don’t know where he is now, whether he has a girlfriend, or about to leave this country (he did mention this last year), whether he’s only looking for something casual, etc. To your other comment, I don’t think I can truly be friends with someone who I already developed a bit feelings for. – Storm Apr 4 '19 at 13:50
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You say you want to ask him if he wants to grab coffee, without disclosing your romantic interests. As LinkedIn's purpose is to tackle professional matters, I'd suggest to keep it simple, something along the lines of:

Hey Bob, long time no see! As you may know, I'll soon leave the company. Would you like to grab a coffee sometimes before I leave?

The "long time no see" indicates you didn't forget about him and would like to keep in touch. Leaving the company sounds like a reasonable thing to meet up before your mission is over, plus it doesn't sound like you're interested in them romantically. Also, as said before, LinkedIn is more about business so I'd suggest you keep it simple and neutral.

Regarding your idea of starting the conversation with:

Hey, long time no see. Thanks for connecting with me. How are you?

it would be a bit weird to me because you said they added you 6 months ago, which is quite a long time. If I were him I'd suspect something. However, maybe just removing the connecting part would be a good way of trying to start a conversation with him and check the temperature - if he seems happy to chat with you then chances are he will accept your coffee invitation.

If he accepts your invitation it may be time to ask for his phone number (to be sure to find him at the time of the meetup).

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  • I still want him to ask for that coffee :) I would prefer to just open the line of communication and see if he would meet me half way and follow up with an invite. If not, probably I will just drop it – Storm Apr 4 '19 at 13:55
  • Okay :) Then I suggest you use the second option and see how he reacts. – avazula Apr 4 '19 at 13:56
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    thank you for the discussion! Another way I was thinking is to wait until I start my new job and update my LinkedIn profile. More of a natural timing to interact and catch up. But it could be months and I don’t want to wait any more... I hope I’m thinking straight :) – Storm Apr 4 '19 at 14:02
  • @Manuki if he had asked for coffee I would have gone along. But he asked for a late night drink in a way that didn’t sit right with me. I think there might be cultural differences in play as well. I’m concerned that directly asking him would give him the wrong impression. But you are right in the sense that it’s my turn to ask. I will proceed with caution :) – Storm Apr 4 '19 at 14:42
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    @Storm if you think there might be cultural differences to take into account, could you edit that info to your question (which cultures, what you're worried might be different)? That way answers can address that part too :) – Em C Apr 4 '19 at 16:14
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I was in a similar situation a few years ago, although not work related. I ended up messaging a woman I had met, using the only available means of communication I had, asking her if she'd like to do dinner. I was absolutely sure she wasn't going to go for it, but figured that at least this way I could say that I had given it a try and get her out of mind. She said yes, we did dinner, dated, moved in together, and now we are very happily married.

So the way I'd look at it is, why not? Right now you have some thought that you might be interested in this guy. As you say, you don't want to have regrets. The simplest, most straightforward thing is to send him a LinkedIn message and say you'd like to get together for coffee (or a drink, whatever your preference). You have absolutely nothing to lose. If he has a girlfriend or a wife, or he's not interested, and he says no, what have you lost? If he's too aggressive, you find that out and you move on.

Another way to look at it is from his perspective. He asked you out for a drink, you didn't want to and said no. He connected on LinkedIn and sounds like you didn't message him at the time. From everything he can tell, you aren't interested. If you want to connect with him, it's up to you to make the move.

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I totally get your point to let him do the first move. [1]

However, as others pointed out, he did two moves so far, yet he did not get a really positive response from you.

So would suggest you send him a casual-yet-warm-&-inviting message. Something like this:

Hey Bob, long time no see! I know it's been a while, but I wanted to thank you for your invitation to connect. As you may know, I left the company. How are things back there? :)

It's a casual(?) message but shows sympathy and interest.

In my own experience, ending with such an open question and a smiley leads to any response. While text on the screen reads icy, the use of one or two smilies can express your feelings and give the reader an accurate idea about the message's meaning.

If he answers with more than two lines, I would say he's still interested in you. You should reply to his response (whatever it is) and end it with:

Keep my number: 123456(your number here)

Once he has your number, as Dr. Patricia Allen says [1], he should do the next move. Hopefully, he'll ask for a coffee!

If he replies with his number instead of texting/calling you, and you still want him to give the first step you may answer:

Great. I'll save you as a contact to identify the sender when you message me.

Not IF, "when you message me". If he does not get that, move on with your life. ;)

Additional tip:

For future contacts, if he asks for a drink again and you feel it as a new booty call, tell him:

That would be nice. I've got this week quite busy, but I have time for a coffee this Saturday's eve. What would you say?

Coffee IS a drink. And's it's OK you suggest this date because he already invited you (for the second time now). So it's not like you're inviting him, but repurposing his invitation. ;)

If he's truly interested in the real you, he will take any chance to spend some time with you and get to know you better.

Do not pick up a bar or pub for the first meeting.

In my experience, arranging the meeting in any nice and quite coffeehouse you find suitable will give the space for the chat you expect to have and will lead to new meetings.

All the best!

[1] I found the book: Getting To 'I Do', by Dr. Patricia Allen to be quite revealing of my own feelings about never starting a pro-dating move. Plus it gives many useful pieces of advice about how to deal with dates. My response was inspired by that reading.

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As I understand it, LinkedIn is something that is primarily used to showcase your résumé and is a useful tool for your career. As such I would recommend not using it to message him on an ongoing basis. I don't know what the rules of conduct on the site are, but if it has more of a professional slant than other social networks like, for example, Facebook then it wouldn't be worth risking your membership of something so useful. Instead, I would suggest you keep conversation light on that platform, swap numbers, and then you can message him via whatever platform you like. This approach will also serve to test the waters - if he is still interested he will happily exchange numbers with you. If not, then you haven't wasted any further time or put anything at risk.

Perhaps start with a work-related ice-breaker like:

Hey, how are things back at [your old place of employment]

See how he answers, then follow up with:

I was wondering if you wanted to keep in touch - could I get your phone number?

If you get his number then text him something like:

I'm glad you wanted to reconnect. Perhaps we could meet up for coffee sometime?

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    "it wouldn't be worth risking your membership of something so useful" Since employee profiles are what makes LinkedIn money, I doubt a bit of casual conversation puts anything at risk. Sure, the guy could report Storm, but I've been reporting the same annoying recruiters for a few years and their accounts are still fine as well. That being said: yes, move from LinkedIn messaging to something more personal quickly. – Jory Geerts Apr 5 '19 at 9:09
  • @JoryGeerts Fair enough, and I admit I don't use LinkdIn myself, but I think the broader principle of "not mixing business with pleasure" is respected by most people and there could be other consequences of using the platform to get a date. – Astralbee Apr 5 '19 at 10:08

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