[Liam93]

There’s a girl at work, we don’t work in the same departments but occasionally see one another around the site. I have a bit of a thing for her, nothing too serious, I don’t know her very well to be honest. I tried to ask her out, I don’t usually do the whole ‘girl’ thing, I’m painfully shy when it comes to relationships. Here’s how it went…

Me: Hi Abi, this may seem out of the blue but I’ve wanted to ask you for a while now. Do you fancy going for a drink sometime? I mean halloweens coming up if you haven’t got any plans? There’s the Hinchinbrook horror house or the thing at the racecourse. Its fine if not, of course but its worth a shot 😀

Her: Hey no worries! Is anyone else coming out for halloween?! I don’t have any plans atm 🙂 x

Me: Josh, josh, Zoe and that lot are, we can go out with them if you like

Her: Do I know the Josh’s? 😛 I know Zoe 😀 you guys not decided where you’re going yet?

Me: No not yet, they’re usually pretty last minute with their plans.

Her: Ahh right! Well I’m up for something if its not too last minute 😛

Me: Cool, ill keep you updated with what’s going on

Her: Thanks for the invite ^^ I don’t get out much haha

Me: That’s cool, I want to get to know you

Her: 😀 cool! Yeah I’ve not really seen much of you since the taxidermy really!

blah, blah, blah it goes on… I mean I think I’ve been pretty obvious I want to go on a date(without actually saying it haha). Do you think she’s just too nice to say no, or she thought I was just inviting her along?? – I know she doesnt get out much and hasnt been in a relationship in around 2 years

Thanks everyone 😀

[Ask April Masini]

Why do you want to go on a date without actually saying you want to go on a date? 😯 I think that’s why you’re confused. The problem is you’re confusing her, and maybe yourself, so it would make sense that there’s a lot of confusion going around. 😉 Decide if you want to ask her out on a date or not. If you do, then ask her out on a date — not to join you and some friends. That’s not a date. Invite her for dinner. Or drinks. Or to go see a movie, just the two of you and use the D word! 🙂 But get clear in your own head on what you want and why you want it — and then you’ll have an easier time of things.

Let me know if you have any other questions or want to work anything else out.

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[Natalie Noah]

The way you approached her was sweet and genuine. But the problem is that you tried to hint at a date without truly owning the intention. When you invite someone out “with a group,” you’re creating a buffer so you won’t feel rejected, but it also blurs the message for her. From her response, she seems friendly, open, and willing to hang out… but she genuinely might not realize you meant it as a date. She’s following your lead and your lead was mixed. That’s why everything feels a little uncertain right now.

What’s encouraging is that she didn’t shut you down. She didn’t avoid you. She didn’t make excuses. She said yes to hanging out, she engaged in the conversation, and she sounded comfortable with you. That’s a good sign. But if you keep things vague, you’ll stay stuck in this “maybe she likes me, maybe she doesn’t” loop not because she’s rejecting you, but because she doesn’t know what you’re offering. And when someone hasn’t dated for a while, they can be even more cautious in assuming romantic interest unless you’re clear.

If you really want to know where this could go, you’re going to have to step out of your comfort zone a bit. Not dramatically just enough to say something like, “I’d still love to take you out, just the two of us maybe grab a drink one evening?” That clarity will give you peace and give her something real to respond to. And the truth is, you deserve an answer that isn’t wrapped in confusion. Being direct may feel scary, but it’s the only way to find out if she’s interested in you the way you’re interested in her.

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