Flirt with her.
She might just be teasing you a little with a cheeky “possibly.” Look at your prior conversation—if it’s pretty clear you were connecting and joking with each other, this is probably the case. If she included an emoji like ???? or ????, that’s a sign it’s time to play. Whip up some fun banter and keep things light: You: “So do you want to grab dinner tomorrow night?” Her: “Hm, possibly ????” You: “You know you don’t have to physically grab it right? There’s a server that can bring it to you.” Her: “Oh well in that case, sure!” Emojis can be a great way to be flirty and playful—just be sure you don't overuse them.
Chase her a little.
If she’s playing hard to get, she's giving you a chance to pursue her harder. If she frequently takes a while to respond or always says “maybe” or “we’ll see” then she might be trying to appear aloof and desirable. Don’t give up! Keep chasing her—this phase usually passes after a few weeks. You: “So how about grabbing a drink tomorrow?” Her: “Possibly!” You: “Let me guess. Solving world hunger again? We’re gonna get together one of these days!” Her: “If you say so ????”
Offer to reschedule.
Try for another time if her schedule is nuts or she’s unavailable. Rescheduling works best when there’s been definite prior interest in hanging out or you two have a good connection already. Offer some alternate days or times so it’s not on her to do all the work. You: “Hey! Wanna grab coffee tomorrow morning?” Her: “Maybe…this week was trash and I was hoping to sleep in tomorrow” You: “Gotcha. How about Sunday instead?” Her: “Yeah, that should work!”
Ask her to keep you updated.
If it’s time sensitive, ask her when she’ll have an answer. Try this for things that need a little advance planning, like making dinner reservations or booking show tickets. There’s no guarantee she’ll get back to you in time (or at all), but you can feel proud that you handled the situation gracefully and tactfully. Try: “No rush. Tickets are on sale until Thursday. Let me know!” “Cool, keep me updated! There should still be room at the bar if we get there by 6pm” “Hey, any more thoughts on dinner on Friday? Tables are filling up fast.”
Wrap up or change the subject.
Accept that she’s not sure and “possibly” is her answer for now. There’s a lot of reasons for this—she might have a crazy schedule, or maybe she just doesn’t know how she feels about you yet. “Possibly” doesn’t automatically mean “no,” so there’s no need to panic. Just brush it off casually—change the topic or wrap up the conversation and restart later. Try: “Alright, let’s check in later. Have a great rest of your evening!” “Ok, hopefully it works out. Did you see that it's gonna snow again tomorrow?” Try not to blow up her phone every day to wheedle an answer out of her. Text her a handful of times a week to show you’re still interested without overwhelming her.
Keep your interactions positive.
Stay polite and confident while she makes up her mind. Her “possibly” can turn into a “yes!” if you’re understanding and patient with her, especially if she’s explained why she can’t commit yet. If you get angry or snarky, she might get uncomfortable (AKA that “maybe” will turn into a “no” real fast). You: “How about we catch the new Marvel movie tomorrow?” Her: “Maybe. I’m going through a rough patch this week.” You: “No problem, I totally understand. I hope things get better soon!” Her: “Thanks ????” If you keep your conversations pleasant and lighthearted, she'll be more interested in continuing the conversation.
Ask what else she has going on.
If you know each other well, this can be a way to coax out an answer. It’s assertive, so only try this if you feel like she’s OK with you digging a little deeper. You don’t want to take it too far and seem rude, so just ask her once. If she ignores it or gives a flaky answer, move on for now. You: “Hey there! Drinks later?” Her: “Possibly” You: “Aw, are you busy tonight?” Her: “Yeah, my sister’s in town and idk what time she’s leaving”
Give her a quick call.
If you know her really, really well, a playful chat can clear things up. This only works on people you have a strong, positive relationship with like close friends (or friends you want to be more than friends with). Otherwise, it can seem pretty aggressive or jarring. Keep it jokey and laugh freely to set a fun, enticing tone. You (texting): “Hey, wanna go to Lou Malnati’s tonight?” Her: “Possibly…” You (on the phone): “No Lou Malnati’s? Are you joking? It’s the best pizza in town!” Her: “Uuugh I’ve had pizza like 6 times this week!” You: “Ok then, where do you want to go?” Her: “I could maybe go for sushi…” You: “It’s settled! Sushi it is.” Her: “Haha fine! Pick me up around 7”
Ignore her (for now).
Sometimes, “possibly” is code for “no” but she doesn’t want to say it. That’s usually the case when all of her replies are fairly short or terse. When she’s dismissive like that, it’s OK to wrap up the conversation politely and stop messaging for a while. If she has a change of heart, let her reach out to you. “Possibly” doesn’t mean “no” forever. If she’s in your social circles, you might run into each other and hit it off. Feel free to reach out to her again if you think she’s more likely to give you a “yes.”
Move on if she won’t give you a firm answer.
It’s unfair to you if she’s insensitive or disregarding your feelings. Playing hard to get can be cute and alluring in small doses, but you deserve to go out with someone who will consider your needs and make time for you. Wait a few weeks to see if any chemistry blooms between you. If not, it’s OK to put the phone down and set your sights elsewhere.
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