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
Dear WORKCRUSH,
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.
If the thought of opening up to someone about this feels daunting, perhaps start small. It doesn’t have to be a deep dive on the first date! Or even the seventh. But once you’ve established a connection and feel safe with someone, sharing this part of yourself can further deepen your bond, allowing them to support and adore you for who you truly are — bra on or off.
Remember, the right person will cherish and respect your needs and insecurities. They will want you to feel as comfortable and confident as possible, underlining the fact that you are beautiful just as you are.
Every step out there is a step taken in self-discovery. You’re embarking on a journey not just to find a partner, but to embrace and love every part of yourself. So, yes, wear your bra if you need to, but also wear your heart on your sleeve. Confidence, self-love and opening up to vulnerability are the sexiest attributes you can bring into any relationship.
Dear Anna,
I was briefly involved with a guy last year. We split amicably due to busy schedules. We’ve since reconnected and slid into a casual friends-with-benefits arrangement. He recently mentioned that he liked my book light, saying how he’d been meaning to buy one for years. Spotting a discounted one at a bookstore recently, I impulsively bought it for him. It was around $7. Yet, now I’m second-guessing the gift, wondering if it blurs the lines of our laid-back situation. I would do this for any friend, but don’t know if it’s too much in this case. — Forward With Boy?
Dear FWB,
Some people do associate gift-giving with a deeper commitment or added expectations, but a $7 book light is hardly a diamond ring. Your gesture is thoughtful and the price is modest, so it doesn’t overstep the boundaries of your current arrangement. It’s a kind and practical gift that reflects a simple act of thoughtfulness, rather than a grand gesture of deep emotional investment.
Given that you’ve mentioned this is something you’d do for any friend, it aligns with treating him with the same casual, friendly regard you have for others in your life. As you can’t have an FWB without the “friend” part — as opposed to a more explicit, late-night-“u up”-text hookup — a small gift like this shouldn’t complicate things.
However, since you’re feeling uncertain, this could be an excellent opportunity to check-in about the dynamics of your relationship and let him know that gift-giving is something you do for your friends. Even if it’s just a brief “hope this is OK” thing. It’s always beneficial to communicate openly about your expectations and boundaries, ensuring both parties are comfortable and on the same page. Remember, maintaining clarity and openness, even in more casual relationships, is key to keeping all parties happy, safe and sane.
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(Anna Pulley is a syndicated Tribune Content Agency columnist answering reader questions about love, sex and dating. Send your questions via email (anonymity guaranteed) to redeyedating@gmail.com, sign up for her infrequent (yet amazing) newsletter or check out her books!)
