Life Advice



Ask Anna: Understanding work crushes, keeping clothes on during sex and FWB gift etiquette

Anna Pulley, Tribune News Service on

Published in Dating Advice

Dear Anna,

I (35-year-old man) struck up a friendly rapport with a lady (unsure of her age, but probably late 20s or early 30s) who works in my building. We find time to converse during breaks and even hung out at a few group events (trivia night, anyone?). On a whim, I invited her to grab coffee with me yesterday afternoon. She agreed, promising to meet me at the coffee shop around 3 p.m. However, at around 2:30 p.m., she texted me to cancel, citing unexpected commitments, but was quick to suggest a rain check and even recommended a popular local cafe for us to try. I'm unsure if I should take her cancellation as polite rejection or whether I should ask her out again. Help would be appreciated. — Wondering Often Regarding Kind Cute Ravishing Unique Sexy Human


Absolutely, ask her out again! Her suggestion of a new place smacks more of genuine interest than polite rejection. Sh!t happens and unforeseen commitments do come up, particularly at work. But, if her cancellations become regular, then it may be time to reassess. For now, give your coffee date another shot.

Dear Anna,

I'm quite self-conscious about my body, specifically my breasts. They just don't seem to match the so-called "ideal" that we often see flaunted across media, and this leaves me feeling less than confident, particularly during sex. In the past, I've found some solace in wearing a bra, as it helps me maintain a sense of control and self-assuredness while being intimate with a partner. However, I can't help but wonder if it's peculiar or unacceptable to keep this piece of armor on. Is it considered unconventional or even off-putting? I’m getting ready to start dating again and wondering what to do if it comes up — mention it beforehand or in the moment or not at all? — Bearing Raw Anxiety


Dear BRA,

First off, it's perfectly valid and normal to seek comfort in what makes you feel confident and secure — yes, even if that means keeping your bra on during more intimate moments. I mean, many of us keep the lights off or low during sex for that very reason.

Let's get one thing straight: There is no "right" way to look or be during sex (or anywhere, for that matter). The media's (and porn’s) portrayal of the ideal body is as realistic as that deepfake of the Pope wearing a puffer jacket. What truly matters is how you feel in your own skin (or in your favorite bra, in this case).

However, while it's absolutely OK to wear your bra if it helps you feel good, consider this a gentle nudge to also confront those insecurities head-on. Not just for potential partners, but for you. Building a relationship with someone new offers a fresh slate, an opportunity to cultivate a space where vulnerability meets acceptance.


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