Help me find the Guy on the Train!

Yeah, this is generally what people use social networking for, nowadays. In answer to your questions: 1. Usually when I get a friend request on a social network for someone I know in real life, but who doesn't have a lot of presence on the site in question, I assume that they just joined and are building their network. Not that they are a stalker. 2. LinkedIn is not for this. It's for professional networking. If you want to know if he's married or see pictures of his kids or find out about his political opinions, that's Facebook. 2a. Conversely, most people don't find it "awkward" to have LinkedIn connections if they are married. Or Facebook connections, really. I have tons of old friends from high school who are now Facebook friends who are married with kids and otherwise not looking to date me. I don't think this is really a thing. 3. People add each other as contacts on social networking sites all the time. You don't need a reason to do it. If you wanted to send him a message, just say "Hey, so this is kind of random, but I think I saw you on Train X from Yville to Zburg last week. I was too shy to say hi at the time, but... Hi! Hope you're well, and I'd love to catch up with you." 4. This is another reason that people use Facebook for social networking among real-life contacts. Because it's meant to sort of be a general overview of your whole life. Some people are judgmental about Facebook and are weird about hearing from an old friend and realizing they're not as cool or successful or whatever, but mostly that doesn't happen. Pretty much anybody is happy to be friends with anybody, as long as they know each other in real life. 5. I don't know, either reach out or don't. The stakes are very low, here. Even if he is the craziest freak who ever insaned, it is unlikely that he's going to come to your house and kill you, or start stalking you, or create problems for you in your life in any way. And if he does anything you don't like via social media, you can just block him or close your account or whatever, because it doesn't sound like you're that heavily invested in it. 6. Again this is what social networking is for. Nobody thinks it's weird to hear from old school friends and the like, nowadays. In fact I just got a friend request from a girl I went to elementary school with, who I haven't seen in probably 20 years, and I was like, "Her baby is so cute!" and not "OMG BACK OFF STALKER", or whatever you're fearing.

You are way overthinking this. Using whatever social media method of your choosing--it really doesn't matter--send him a message that says, "hey! Saw you on the train to Walla Walla last week and thought I'd say hi. Hope you're doing well!" You're saying hi to an old acquaintance. You're not proposing going on a date with this man or being a homewrecker or flirting with him or whatever other story might be built up in your head after a week of fixating on it. You're just saying hello. That's all! It's cool! Easy! Have fun!

Well, you're probably romanticizing him a bit. It's not a big deal to reach out a week later. "Hey, saw someone who looked like you on the train last week - how have you been?" Do it on Facebook if LinkedIn feels weird. It sounds like you have a lot of thought-out reasons for why neither works for you, but I wonder if you are creating roadblocks for yourself so you don't actually contact him. What's the worst thing that could happen? He will just not reply? Oh well. He'll think you're weird? Well, you've seen him once in ten years so you have awhile to go before you have to interact with him at best. He's married? Bummer, but it's good he's happy and no harm no foul. If you want to do this, do it. If things about it are hard, make a game plan. No need to respond to 50 friend requests. No reason to look at Facebook for anything more than friending him, asking him for a drink if it goes well, and then moving off to email ("I don't use Facebook often but lets continue this catching up on email. Here's my address." - and let him reply that way if he wants. If not, oh well.) Don't invest too much in this. He is just a guy that you were flirty with when you and he were both young. It might go somewhere, it's more likely that it won't, but you'll never know if you don't try. Just don't get too invested too early - be slow and evaluate him and how you feel at all points. I might even suggest that if it is causing you this much anxiety that maybe you should work on that before you try to date. Best of luck to you.

Ugh, no, don't get a LI account just so you can connect with this rando guy from your past. That's not what LinkedIn is for. Either get over your Facebook dread and friend him there, or chalk it up as two ships passing in the night. I think you're in fantasy mode right now, which is fine, but I don't understand exactly what your motivation is here.

He may have already checked you out on Facebook and sent you a message! Log in!

Suggestion: have someone you trust log in to Facebook for you. All they have to do is click into the friend requests, the inbox, and the notifications flag thing one time each, and it'll clear out the million "new thing" notifications you have. At least for me, as long as the friend request flag isn't lit up red with a number, it's easy not to click on it and just to ignore it. I dunno, maybe if you have a REALLLY trusted friend you could have them cut and paste a message you email them (for Train Guy) and send it to him. The message would end with "if you want to drop me a line, I don't use Facebook much so just hit me up at [email protected]" or whatever. Bam. You never have to log into Facebook and you've contacted him and put the ball in his court. It's kind of elaborate but if you really need to not log in to Facebook yourself, it's a thought.

Even though you hate it, Facebook is the right tool for this job. The message is something like, "Hey, I'm not sure you'll remember me, but I think I saw you on the train to Funkytown last week. Sorry I didn't say hi. I wasn't sure it was you until you got up for your stop. Hope all is well with you." He'll reply or not.

I wouldn't set up a LI account just to contact him, that would be weird. This is exactly what Facebook is for. He wouldn't find it weird to hear from you on FB, even if you hadn't maybe seen him on the train last week. Say hi on FB, or get over it and move on with your life.

Before you go any farther, decide what you want from this--- do you want a buddy? Do you want something more romantic? And don't forget, he appeared to recognize you but chose not to say anything anyway: perhaps, just perhaps, that wasn't shyness or awkwardness, perhaps he simply didn't WANT to reconnect with you --- YOU may have viewed your high school interactions as a fun flirtation, but how did HE see it?