Ask Elliot: Man Repelling & Every Guy's Least Favorite Question

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Our resident relationship/men's fashion/straight-guy-gives-advice guru Elliot is taking on your personal quandaries and giving you his answers. Check out the second round of Q&As below and be sure to send your own questions for Ask Elliot to submissions@refinery29.com.
Do men ever, ever answer honestly when you ask "How do I look"?
Dear Linda Looks,
There's the small questions and the big questions when it comes to asking for your dude's feedback. "Do you think I should wear the blue booties or the red flats?" is much less loaded than "Do I look cute today?" Only a true creepasaurus would tell his girl she doesn't look cute, so if you want his real opinion, better to ask about a specific item like a jacket or hat. Keep it quick if either of you are late, hungry, or hungover, though. Every one looks way cuter after they've eaten.
How can we talk openly about our romantic past without offending/making it super awkward? I feel like it's important to talk about, to get to know each other, but I don't want to be weird.
Dear Patricia Past,
Your instincts are correct. Showing that you have been in relationships before will humanize things for everyone. A smart lady uses memory-lane sessions about her old exes to slyly tell her new man what she likes and wants. Small fights of smack talking are a good, chill way to break the ice. Saying he ruined your life, however, is just sad. Don't do that.
Bringing up a former flame's good qualities prevents you from sounding bitter, but don't go on at length about specific, very personal stuff.
Pro tip: When you're starting out, try to center the conversation around "types of people" you have dated, rather than specific individuals. After some trust has been earned, he can learn that "the Banker dude" was in fact named Chad. Until then, he can just be a character you are sketching out.
What's the deal with "man repelling"? Are there any particular trends I should avoid if I'm trying to make a good first impression?
Dear Rachel Repeller,
To my understanding, "man repelling" is wearing expensive, ugly, or wack stuff that winds up looking super-cool or maybe terrible. A lot of cute girls seem to be doing it. I dunno. I'm with it as a concept; although, I don't know much more about it.
As for keeping up with current looks, it's always good to give a subtle indication that you know what's up. If that means not wearing boot-cut jeans to you, that's cool. If that means wearing a color-blocked dress with printed creepers, that's cool, too. I'm not sure about specific trends, but don't wear uncomfortable shoes on your first date. I mean, don't wear your "comfortable shoes" either. You know what I mean.

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