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Hard to Say is This Recording’s weekly advice column. It will appear every Wednesday until the Earth perishes in a fiery blaze, or until North West turns 40. Get no-nonsense answers to all of your most pressing questions by writing to justhardtosay@gmail.com.

Hi,

How long should you wait before explaining your feelings to a woman who recently got out of a long term relationship?

Before my friend Ava went away to the Peace Corps in Africa, we talked about maybe starting to date. She met someone over there and although we exchanged a few e-mails, I was pretty bummed about it. Now she's back in the U.S. and her facebook says she's single. Is it too soon to ask her if she's interested in picking up where we left off?

Timothy E.

Timothy,

You should never ask someone for something that you could just as well start doing in order to know her answer. If you want to go on a date with Ava, by all means offer to take her on one. If you wait, there's a fairly good chance someone else will get there first, given her magnetic personality and propensity for world travel. 

It is probably best to recreate the circumstances of her initial attraction to you, however. If you come on too strong it feels preordained. Try reconnecting with her again and slowly begin suggesting she rely on your affection. Next stop: codependence!

The real risk is in becoming a shoulder to cry on. Do not console her about her past relationship, unless it is in insightful cracks about the size of the guy's dick or what a dick he was. Make it seem like you were living your own life while she was gone: although let's face it, you weren't.

Hi,

I get along super-well with a guy I work with named Yan. I'm not really the type to approach a guy, but we have such a great connection and really lean on each other in workplace social settings. He's been really helpful in my career as well for a number of reasons. 

To me it would be worth risking our work friendship if it led to something more. I'm having a hard time thinking of a way that I can find out if Yan is interested in becoming something more without changing the way we interact with one another. Do you have any ideas?

Jennifer G.

Dear Jennifer,

If Yan is doing you all these good turns, it is quite likely he feels the same way. I wouldn't be that nice to someone unless they honored me with their massive fortune.

Getting him to make the move should be easy. Just hang out as friends. Eventually, any man will begin to develop feelings for you. Drop classic, time-honored lines like, "Yan, you're such a wonderful friend." "You would be a great boyfriend for someone — not me, I just mean a hypothetical other woman." Deep in the recesses of his animal brain, he will start to say to himself, I have done everything for this woman. There must be a reason. 

If necessary, invent a fictional, long-distance boyfriend who is really wanting to see Doctor Strange. Then give me his number.

Illustrations by Mia Nguyen.