Dear Lila Pearl,

How do you know when something is a date or just a dinner engagement between two friends? I’ve shared several meals with this male friend of mine and I still can’t tell if we’re dating or not.

—Helplessly Hoping

Dear Helpless,

A tricky question, if there ever was one. There are various conventional signs to look out for which might key you into the datiness of a meal: Does the man pay? Is there awkward flirtation? Hand-brushing when reaching for the pepper? Sex in the bathroom between the fois gras and the pear tart?

But there’s only so far convention can take you. Often, dates only become clear retrospectively. Says Susan, aged 50, “It was only after Jim and I had been married for four or five years that we both fully realized the significance of our early meals together. Of course, it took Jim much longer than it took me.” One way to work around this problem is to take matters into your own hands. Next time you’re out for dinner with your man you might say, “Pass the salt, Matt, inasmuch as this is our fourth date.” Or “The soup is excellent tonight. Gosh, food always tastes so much better when two people who are romantically inclined decide to eat food together in a quasi-romantic setting.”

Best of luck.

Suggestively,

Lila Pearl

Dear Lila Pearl,

My ex-boyfriend and I were chatting online and he asked for my new phone number. I gave it to him and then he called, but I failed to reach my phone “accidentally.” How much of an asshole does it make me to not call back but keep chatting online? And how much MORE of an asshole does it make me to tell him I didn’t answer because I’m in another boy’s room and not explain why? Or to sign off and just pretend I fell off the face of the Earth?

—Delila M. Pizzazer

Dear M,

A maiden walked many weary miles until at last she came to the mountain of ice. She entered the cave and walked to the chamber of fire. The heat burned her and she was frightened, but entered. “Salamander,” she asked, “do you know of a kingdom east of the sun and west of the moon, and do you know of a youth who is to marry the troll princess there?”

The salamander sighed, and a wisp of flame scorched the maiden’s slipper. “I know what is in your heart and in the heart of the youth, and I know your hearts are breaking. But this kingdom does not lie within the fiery heart that I know. All I know of this kingdom is that it is east of the sun and west of the moon, and if you reach it you will not find a welcome within.”

As far as Lila Pearl can tell, within the bounds of etiquette, it’s unkind to tell someone to call you and then not answer your phone. But let’s move beyond questions of etiquette (so there is a beyond?) Sadly, LP is no salamander, and she knows quite well the kingdom of Exhood, lying north of We Broke Up and south of Therefore We Must Make Each Other Suffer. But why not go the icebox instead? And make yourself a nice sandwich?

If you’re trying for a friendship, the way to get there is not by alternatively ignoring him and toying with him. If IM is okay but phone chat isn’t, make that clear. If you still love him, let him know. If you don’t, let him be. The lonely kingdom is rainy this time of year (and every time of year), and the service in the outdoor cafés is terribly slow.

Patiently,

Lila Pearl

Dear Lila Pearl,

I have a problem, which I doubt even you can solve, but your advice has amazed me in the past and for that reason I’m counting on you now. My problem is that I’m honest-to-goodness, head-over-heels in love with my professor. Although I’m not in her class at present, I am in frequent contact with her, and every time I see her it’s like my heart is being ripped out of my chest. She’s married, and I don’t think I have a chance. Should I keep pining? Should I try to give her up cold turkey? Should I make my move??? I don’t want to ruin anyone’s life, least of all mine. You’re my only hope.

Love,

Pathetic in Pink

Dear Pathetic,

If you like your heart where it is (planted firmly behind your ribcage), Lila Pearl would advise: Leave your professor lady and never look back. On the other hand, if you’d prefer a sort of Temple of Doom-style heart situation, by all means keep pining.

Precisely,

Lila Pearl

Got a question? E-mail Lila Pearl at lila@uchicago.edu.