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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