“Ask Anna” is a sex column. Because of the nature of the topic, some columns contain language some readers may find graphic.
Dear Anna,
I am a 25-year-old male and have been recently getting closer with a woman around my age. We’ve been spending more time together lately, both in group settings with mutual friends and privately. I started developing feelings for her and I believe she might have the same feelings for me. I don’t want to rush things or make them awkward with our friend group by confessing my feelings prematurely. But I also don’t want to miss a chance if she feels the same way. When’s the best time to shoot my shot? — Making Overt Validation Exciting Sucks
Dear MOVES,
As is so often the case, the best time is now. If she feels the same way, great! If she doesn’t feel the same way, then expect a little awkwardness, but it’s not going to alter or ruin your squad group — especially if you act cool about what happens.
While I wish it was otherwise, there’s no definitive way to know if someone likes you — you just gotta ask them. But if you’re looking for clues to bolster your bravery, here are some general guidelines to parse when someone might be into you.
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Observe her body language and signals: Pay attention to her behavior and subtle cues, such as increased eye contact, touching your arm or shoulder, signaling you out in the crowd, texting you for no reason and leaning in when you talk. These signs could indicate that she’s interested in you romantically.
Create opportunities for one-on-one time: Plan activities or outings where it’s just the two of you. Is she receptive to these hangs or hesitant? Does she flake or cancel often? Does she initiate back? These are signs to pay attention to.
Deepen the conversation: When you talk, shift from casual chats to more personal topics, such as your dreams, values and future plans. Gauge her comfort level and whether she’s opening up and reciprocating. This could show that she feels close to you and may be ready for a deeper connection.
When you do ask her out, make sure you’re alone (i.e., not out with all your friends) and preferably not in a public place — just in case you need to make a swift, ungracious exit. If things are vibing, you could say something like, “I’ve really enjoyed spending time with you and have developed feelings for you. I’m curious to know how you feel about me?”
Remember that every person and relationship is different, so there’s no one-size-fits-all answer. Trust your intuition and let the development of your connection guide you. Be prepared for any outcome, as she might need time to process or might not reciprocate your feelings — if that happens, it’s OK! Because then you know not to waste your time pining anymore and can move on to someone else.
Be brave, MOVES, and remember: As George Addair said, “Everything you’ve ever wanted is sitting on the other side of fear.”
(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!)