I’m leaving my dating options open in my city, but I thought I’d try this too and see what happens. I don’t plan on moving back to my home state and it’s rare that I’ve been home when Peter is visiting my brother, so I’m not quite sure how else Peter and I would get together. The last time I saw Peter was two years ago. I also figured that cold-emailing him is just like online dating, but in this situation I know him and have met him before. Peter has always been in the back of my mind as a possibility, so I was thinking, what if?
What do you think about my e-mailing him? Is it a bad idea? On the one hand, I don’t think it is and there’s always the possibility it could turn into something, but on the other hand, Peter could think it is really out of the blue (which it is), say something to my brother and then I’d have to have an awkward conversation with my brother. If you don’t think it’s a bad idea, do you have any advice for what to write in the first e-mail? — Cold E-mail
It’s not necessarily a bad idea, but going about it the way you’re planning to does pose some risks and lots of potential awkwardness. First of all, cold-emailing someone you haven’t seen in two years, whom you’ve never emailed before, whose email address you tracked down on a school directory, and with no excuse at all isn’t quite like online dating. Not at all really. People on a dating site are actively seeking someone to date; for the most part, they’re welcoming emails from potential matches. At the very least, they’re prepared for them and have put themselves in a position to receive them. That’s not the case with Peter. He doesn’t know you have his email address, he hasn’t seen you in two years, he’s not expecting to hear from you, and, frankly, might wonder why, all of a sudden, you’re sending him an email asking how’s doing. You’d be better off if you had some excuse to contact him — like brainstorming a gift for your brother, asking a specific question about medical school for a “friend” who’s considering applying, or seeking advice on a topic he knows something about (for example, if he’s an extensive traveler, you might ask him for vacation suggestions). The point is, you need some excuse to contact him besides just wanting to say ‘hi’ when you’ve never really said ‘hi’ to him to outside your brother’s presence and you haven’t seen him in two years.
And speaking of your brother, it’s a pretty risky move to reach out to his best friend behind his back. It makes what you’re doing seem suspicious — the whole looking up Peter’s school email address in his school directory instead of just asking your brother for his personal email begs the question: “What are you trying to hide?” Why not just ask you brother for it? Unless you think he wouldn’t approve, in which case, you might want to talk to him about your plan before creating potential drama between you. It’s a good idea to give him a head’s up even if you’ve already decided you’re going to go for it whether you’ve got his blessing or not. And for all you know, he would approve and he may have some helpful insight for you. Maybe he can provide you a good excuse to reach out to Peter or advise you on how to compose an email that won’t seem completely random. If he’s a really nice brother, he might even play matchmaker and put in a good word for you with Peter. Hey, anything’s possible, right?
*If you have a relationship/dating question I can help answer, send me your letters at [email protected] and be sure to follow me on Twitter.