When you really need a favor from someone you haven't talked to for a while, reaching out can be awkward. Re-break the ice by sending them an email with a clear subject line, like "Reconnecting." Early in the body of your email, acknowledge that some time has passed since you last spoke, and briefly update them on what you've been doing professionally. This will provide useful context for your request. Then let them know what kind of help you need. You want to sound friendly and confident that your request is something they'll want to say yes to. But give them an easy way to say no, and offer to return the favor either way: "I'm sure you're really busy, so thanks in advance for considering it. Please let me know how I can be helpful to you, either now or in the future." And then stay in touch — that way it won't be awkward the next time you want to say hello.
Adapted from "How to Email Someone You Haven't Talked to in Forever," by Rebecca Zucker
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