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How should I re-initiate communications with him and build up rapport to make this happen?

Tagged as: Crushes<< Previous question   Next question >>
Question - (28 April 2013) 2 Answers - (Newest, 30 April 2013)
A female New Zealand age 36-40, anonymous writes:

Dear Cupid,

I've lately rekindled attraction for a middle school crush but not contact. We're in our late 20s now and haven't seen each other in 14 years, but we're on each other's Facebook (he added me first years ago, despite havign ignored me as a teenager). He rarely updates but there are signs that he logs in frequently. We had a long chat that he seemed to enjoy a little more than a year ago, and he told me that I should let him know if I'm ever in his town--which I'm planning to be a couple months from now on a business trip.

About feelings... I'd say I'm not in love and not considering any serious relationships with him, but I definitely am attracted and don't think we'd be friends if we had the opportunity to see each other more often. We're both single but live a few states away from each other, and keep each other at a "safe emotional distance" in case any one of us is in a relationship with someone else.

One of the reasons I've been thinking about him lately is because I got on board a long term project which may require me to interview his parents on the other side of the country. I haven't been in contact with them, nor do they know about this project yet, but they happen to be experts in the field I will be researching and have a unique professional history with just the right credentials for it.

I tried PM-ing him on Facebook about it last month (though I didn't mention looking for his parents, instead mentioning that I just attended a middle school reunion with our mutual friends and that I'm currently applying for jobs--the one that lead to this project he doesn't know about) but he didn't reply. Although the PM indicated that the message was read.

Obviously, I want to keep things businesslike and professional as far as the parents are concerned, but I really want to flirt with their son and keep it as a "one-off thing" and our little secret.

My current goal is to score an afternoon coffee date with him and get some intellectual conversation going on, because that's what we both enjoy. And if that works out then I'd like an additional daytime date on a Saturday hunting photos on our SLR cameras in some nice landmarks in town (we both enjoy practicing amateur photography). I want to come across as polite, respectable, and elegant, but at the same time turn on as much sexual tension as possible. I want something physical to happen--a kiss would be great, but hand-holding or hugs would make my day too--but I want to either lure him into initiating or to make us both comfortable enough for me to "steal".

How should I re-initiate communications with him and build up rapport to make this happen? Does my unreplied PM from last month make things awkward? What are some do's and dont's in warming up contact, considering that we currently live in different states, work in different industries, and normally just don't talk to each other?

View related questions: crush, facebook, flirt

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A reader, anonymous, writes (30 April 2013):

OP you say it could be creepy if done wrong, and is possible "embarrassingly childish" and that you know your going to be embarrassed if your former school friends your still in touch with find out.....so why do it?!

"he was the first guy I ever liked, so I think there's always going to be a part of me that wants to make him fall for me and go, "Ha! So you do find me attractive after all!" Op that sounds quite desperate, needy and insecure in all honesty. What difference does it make if he did or didn't find you attractive when your were a kid? Your not the same person now! Are you willing to risk making a fool of yourself, being hurt and humiliated and so on for the sake of proving something to yourself that's being eating away at you for 14 years???

OP this is so silly im sorry. He could be married, gay, going thorough a divorce or impotent for all you know. He's not the same lad he was all those years ago.

Your talking about "fooling around" with this guy....I dont want to sound rude but that's what I would expect a teenager to say not a grown woman. Fooling around is kids stuff, this guy is a grown adult man now.

So what are your intentions? To fool around after meeting his parents (on the pretence that they are the only people who can assist you in your work or studies) and then walk away feeling smug because you can satisfy your feeling that he fancied you all those years ago at school?!?! IM sure he would really appreciate that.

I'm also sure that your friends and family would not be best pleased with you if they found out either. YOu need to move on OP, this is crazy!!

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A reader, anonymous, writes (29 April 2013):

This is verified as being by the original poster of the question

Thanks Zippy,

I agree and am fully aware that my current attraction to this guy from 14 years ago is mostly based on fantasy, and that in real life we really don't know each other much at all. Still, that doesn't change the fact that I want to see him in person just once, just to see how much of that fantasy I actually got right, what I got wrong, and put it to rest.

Perhaps there's a little part of me that kind of wants to make up for the fact that we didn't get together as kids--he was the first guy I ever liked, so I think there's always going to be a part of me that wants to make him fall for me and go, "Ha! So you do find me attractive after all!"

I know that's embarrassingly childish, and probably can turn a little bit creepy if played the wrong way, but it's a feeling I can't help. I guess the reason why I want to keep it hush hush is because I'd be mortified if my middle school friends--who I still see once or twice a month--find out that I'm interested in how this guy's doing. And he's not even that great looking, and my friends think he's really boring (though I disagree...he's just has different interests that I happen to be interested in myself, and most people don't get it).

I do think the fact that he didn't reply to my PM from last month is telling. I don't rule out the possibility that he may not be interested in me, but then it could also be that the message's timing could be better, or that I contacted him for the wrong reasons.

LOL no, of course I have not brought up any romantic overtones in a Facebook PM!

The message I sent him simply said "hey, just caught up with our mutual friends in a class reunion this weekend and your name briefly came up in a conversation so just thought I'd shoot a quick hi...by the way I'm in the middle of a career change and applying for jobs in a different industry, including companies based in the city you're living in...if you happen to know people in that industry I'd appreciate some introductions...hope you are well." So no there hasn't been any creepy discussions about kisses, cuddles, or even a date.

Alternatively, I'm wondering if I should do the opposite of your advice and skip contacting the son and just go straight ahead to contacting his parents as professional contacts. I have met his parents before and they remember me, so I think as long as I'm not fooling around with their son I have every legitimate reason to contact the parents in a professional context and get down to business, get my work done. But if I see the son first and fool around with him, I think that's what would make seeing his parents awkward, whereas the reasons why I would even bother contacting his parents are purely business--I would contact them anyway even if I didn't fancy their son.

Then when business with the parents is done and over with, and I'm still interested, maybe I can rethink contacting the son again and seeing how it goes. After all, then I could say "Hey, I met your parents over business for this project about so and so. Heard good things about you from your parents, and let's catch up on my next trip." Does that sound more reasonable?

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