When to ask her out: The acquaintance
An acquaintance is somewhere between a stranger and a friend. It’s someone that you speak to on a regular basis but don’t necessarily communicate with outside of a recurring situation. An acquaintance is the waitress at the restaurant that you go to all the time, or another student in a class you’re taking, or a co-worker. The key is that you don’t really know these people personally, you know them through some activity and don’t really see or interact with them otherwise.
Acquaintances are more difficult to ask our than strangers. With strangers, you’ll never see them again so there is little risk in asking them out. With acquaintances, you know that you’ll run into them again and that can cause stress. After all, if the acquaintance says no, you know that you’ll be seeing him or her again soon. With either a yes or a no, though, you run the risk of changing the dynamic of the situation.
Consider the situation of taking a class. You’re there on the first day and a girl walks in that is absolutely beautiful. If you ask her out right then and there and she says no, you may not want to go to the class anymore; if she says yes, your new relationship may become a distraction for the other students. So what do you do? Simple, you wait. An acquaintance actually gives you time to get to know them. Strike up a conversation each time you’re together, gradually learning about the other person. Invite the person out in a group with others from the same situation, i.e., suggest to everyone that you go out after class for a drink. Get to know the other person as much as possible through your shared moments, an opportunity you don’t get with strangers.
The best time to ask out an acquaintance is when you aren’t sure you’ll see them again. The class may be coming to an end, or the waitress may be changing jobs, and if you don’t do anything, that person will walk out of your life possibly forever. Now is the time to act. This way you’re assured of two things: 1) you won’t ruin the dynamic of the situation and 2) you won’t need to run into this person again if they say no. Invite him or her out, just the two of you. Make it clear that you’ve enjoyed their company and conversation to this point and would be severely disappointed if you lost that. After that, you’re on your own.
Note about co-workers: you may need to wait longer and have more “group dates” before officially asking out a co-worker. Make sure you fully understand your company’s dating and sexual harassment policies before even thinking about it. Most companies forbid relationships between managers and their subordinates, but some also exclude fraternization of any kind or may even have love contracts.
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