I have had the unique opportunity to provide consulting services to a relationship company, helping them improve their communications. As part of the process I've learned a lot about their first meeting they hold with their clients, during this meeting they give first date suggestions, including:
An article from

The Right Way to Make a First Impression: Social, Mobile, & Email
1) Look sharp, act confident and speak clearly
2) Engage in a back and forth dialogue - ask, then tell
3) Pay attention to what your date is saying and doing
4) Don't get distracted by outside influences - focus on your center of attention
5) Don't forget to say Thank You
Digital marketers can also learn from their first date advice, one could even compare those first messages as first dates, because:
1) You have to make your messaging crisp - your content needs to grab the recipient's attention and you need to clearly tell the recipient why they are receiving your email.
2) Ask the recipient for their preferences, this can be done by their click patterns or when they complete a short survey - keep them engaged and serve content relevant to their interests.
3) Pay attention to what the recipient does after they provide their preferences for example, if they said they liked the sports section, did they actually go there? You must tie your analytics.
4) Keep the content focused so that the recipient isn't distracted, allow them to clearly focus on their items of interest.
5) Be grateful and send them a note asking them to give you feedback on the first email - was it what they wanted? Was there something else you could offer?
Digital communication channels are private and personal, so remember that you have the privilege of communicating with them - after all, it's your first date!