[Steven22]

Hi April, There is this girl i work with, not in the same office but close, she is very shy and everybody knows that and it is hard to get her to talk, but we had a few talks and started chating online via Facebook, i intiated the first chat but then there were plenty of times she did it, now for the last two weeks we chat 24/7 all the time like we have been a couple for long time, we talk really relaxed and right about everything we send each other hearts and thoose kissy smileys. Now when ever i see her at work she smiles at me but is very shy to intitate contact, and i really dont know what to do, should i pursue her, Because she doesnt have plenty of friedns and she told me how she was in a bad relationship before and i know everything about her. But now i am in dilema maybe she sees me just as a friend or maybe she is just bored because she doesn have many friends and i take her time. Because i told her once to go out and she said she “feels” bad and i know this wasnt the case, and next time i told her there was a good movie in cinema so we should go and she was smiling and changed the topic. Now i had girls before but they were always open when i asked them to meet, but with this one i actually never met outside of work, but we chat and talk all the time online, one day we chatted until 7am and went directly to work. So i really dont know, because i am afraid if i ask her out or something more serious she will fled.What do you suggest me? Thank you

[AskApril Masini]

You have to change the dynamic in the relationship. You’re in the friend zone because you’re treating her more like a friend than a girlfriend. 😉 You have to be the one to act like a boyfriend, not a friend. So ask her out on a date — and if she won’t go, be disappointed, but do move on. If she sees you’re not going to be her friend and are really interested in her as a girlfriend or a date, she can make the choice to be that person or not — but when you’re offering her friendship you’re helping to create the situation you’re in (and don’t want to be in!). Besides, women like men who are popular and successful at dating, and if she sees what she’s missing out on, she may be more interested in you. So, yes — do pursue her — but not as a friend. Be the guy who gets the date, not the friend zone. 😉

[Sally]

This is one of those situations where the connection is real, but fear is running the show probably for both of you.
From what you’re describing, she likes you. People don’t stay up until 7am talking, send hearts, and chat nonstop if they’re just bored. That’s emotional closeness. The issue isn’t interest, it’s anxiety. She’s shy, she’s been hurt before, and meeting in person makes it feel real in a way online doesn’t.
Here’s the key thing: don’t keep living only in chat land. That’s safe, but it’ll slowly drive you crazy.
Instead of asking her out in a big way, make it small and low pressure. Coffee after work. A short walk. Something with an easy exit. And say it calmly, once. No pushing.
If she pulls away, that’s not you doing something wrong. That’s her not being ready.
But if you never ask again, you’ll always wonder.

[Tara]

This is not a romance, it’s a digital comfort zone, and you’re stuck in it because you’re afraid to risk rejection.
She’s not “mysterious.” She’s not “too shy.” She’s enjoying attention without commitment. Endless chats, hearts, kissy emojis, all-night messaging that’s emotional stimulation with zero accountability. If she wanted to see you, she would. Shy people don’t magically lose their shyness online and then regain it only when real effort is required. That’s not shyness. That’s avoidance.

You already asked her out. Twice. She dodged both times. That’s your answer. When interest is real, people don’t deflect; they find a way. Changing the subject is a polite no. Smiling at work while refusing real-world interaction is how someone keeps the benefits without escalating.

Right now, you’re her emotional crutch. You fill her loneliness. You make her feel wanted. You’re safe, available, and low-risk. And because you keep talking without drawing a line, she has no reason to move forward. You’ve made it comfortable to stay exactly where you are.

You’re also lying to yourself about being “afraid she’ll flee.” She is already just slowly, passively, while draining your time and energy. The longer you play along, the worse it gets.

You stop the fantasy. You ask her out one last time, directly, no soft wording, no excuses. If she avoids again, you pull back completely. No late-night chats. No hearts. No emotional boyfriend behavior without an actual date.

[Member]

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