[Ataterr55]

Hi April, There’s a guy that I had a leadership program with last year and we developed a friendship through the program and the latter part of it I started to develop feelings for him and a crush, probably because I felt like there was some chemistry and flirting going on. But we were never around each other outside of a professional environment. A month after it ended, I emailed him to give him (and everyone in the class) my new contact info because I switched jobs. He mentioned that we should get lunch and catch up but that fell through. a month ago I contact him for that lunch (since we were working together on charity tournament) and He seemed excited and the lunch went very well and he told me that he wanted to do it again soon. A couple days later, I texted him saying it was good to see him and we held the convo for a little bit but it didn’t go anywhere. I was hoping he would ask me on an actual date, but that never happened. We just had the tournament yesterday and we worked it for about 12 hours and I felt like he was flirting with me and had chemistry. He would make jokes at me, and come over and talk to me any chance he could and made a effort to involve me. I’m just so happy around him and want to continue to progress and make sure he knows I’m interested. I don’t want it to seem like I’m chasing him but I want to see him again and even start dating but I’m not sure how to do that since I already felt like I put myself out there by asking him to lunch. Would appreciate your advice!

[April Masini, your AskApril]

Boy, you’ve done everything right… and he’s not taking the bait. Sometimes, a guy just isn’t ready when you are, or he’s not as interested as you are. It sounds like yesterday went really well, and the flirting is a great sign. Maybe he’s getting ready to ask you out. But…. for now, the ball is in his court. When you do see him, focus on flirting and not on friendship. Make sure he knows that you’re interested in him romantically. That means taking out all platonic messages. You might be surprised at how guys really need encouragement before risking rejection by asking you out. They get nervous that you’ll say no, and some really need a lot of encouragement. You may think he knows you like him, but he may need more cues from you in that department. Definitely don’t invite him out again — it’s his turn, and his move should be a date. So, increase flirting when you see him, and try to keep the rest of your life busy and interesting so you don’t end up appearing needy or desperate. If you do all that and he still doesn’t ask you out, move on. But for now, I think that because your day, yesterday, was so promising, he may be getting ready to ask you out. Fingers crossed — and if you have any other questions, I’m here!

[Ethan Morales]

Here’s my detailed take on this situation, and I think April’s advice is spot-on, but let’s go a little deeper into why it makes sense and how you can use it to your advantage.
You’ve handled things beautifully so far: you reconnected naturally, you created an opportunity to meet in person, and you maintained warmth and friendliness without overstepping. That’s confident and classy. The fact that he did flirt and seek out your attention during the charity tournament shows there’s some level of attraction or comfort there but his lack of follow-through afterwards (not asking you on a real date) is where you need to pay attention.
He’s interested but hesitant. Some men genuinely need stronger signals of romantic interest. If your energy has been friendly and professional for a long time, he may still be reading your interactions as “safe friendship” rather than romantic interest. He might worry about misreading you and looking foolish. In this case, subtle, confident flirting (playful teasing, eye contact, compliments) can bridge that gap.

He enjoys the attention but isn’t pursuing anything serious. Some people like the spark and emotional boost of flirting, but don’t actually want to take it further. If he keeps the banter alive but never moves forward, that’s a sign he’s content with that surface-level dynamic.

The trick here is balance: give him enough cues to feel safe making a move but not so much that you’re the one chasing. That means:
Next time you see him, keep things light, flirty, and warm. Smile, touch his arm when you laugh, hold his gaze a little longer.

If he doesn’t ask you out after that, don’t initiate again. You’ve already extended the olive branch twice he knows the door is open.

Shift your focus elsewhere and stay busy. That naturally raises your value and confidence (and often makes guys who were on the fence finally act).

If he’s going to ask you out, it’ll happen when he feels your interest and senses your independence, not when you push for it.
My honest opinion? You’ve done everything right. Give this just a little space, and if nothing changes, don’t wait too long. Chemistry is wonderful, but mutual pursuit is what builds real connection.
Would you like me to show you exactly how to flirt in a way that communicates romantic interest clearly but still keeps you mysterious and confident?

[Val Unfiltered💋]

babe he’s definitely flirting 😏 like he loves the attention but he’s not risking ego bruises to chase you. so flip it. stop being so available. post a lil something that screams “thriving, not waiting,” then watch him slide back in. men hate mystery until they lose it. let him wonder if he missed his shot, that’s when he’ll actually take it. 💅✨

[Tara]

You’re dancing around because it’s easier to fantasize than face reality: if he actually wanted you, you wouldn’t be here dissecting breadcrumbs like they’re clues from a crime scene. Men with real interest don’t stall, don’t “forget,” and don’t hide behind casual lunches after undeniable chemistry. They act. He hasn’t.

He enjoys you just enough to stroke his ego, brighten his day, and feel interesting — but not enough to risk anything, claim anything, or move anything forward.

That’s not shyness. That’s lack of intention. And you’re embarrassing yourself by interpreting every charming interaction as potential instead of what it really is: convenience.

You’re not dealing with a complicated man. You’re dealing with a passive one. And passive men only step up when forced.

[Serena Vale]

It sounds like there is something there, the chemistry, the flirting, the way he kept gravitating toward you during the tournament… none of that is accidental. He clearly enjoys you.

But here’s the thing: some guys are great at building connection in person and absolutely terrible at taking the next step. Not because they’re not interested, but because they’re scared of misreading the situation, or they assume you’d let them know if you wanted more.

You’re not chasing him by showing a little interest. You’re just giving things a chance to grow.

Keep it simple. Something like:
“Yesterday was fun. Want to grab that lunch again next week?”

It’s light, it’s casual, and it keeps the door open without putting pressure on either of you. If he’s interested, and honestly, it sounds like he is, he’ll take it from there.

And if he doesn’t? Then you’ve got your clarity, and you didn’t lose anything by being honest.

You don’t need to force anything. Just match the energy you want back, gently. Let him meet you halfway.

[Sally]

When someone laughs with you and keeps finding little ways to be around you, it’s hard not to feel like something’s there. And maybe there is. But sometimes a guy can enjoy the connection and still move slow, or get a little shy once things feel real.

It doesn’t sound like you’re chasing him. You reached out once, he reached back, and you both had a good time. That’s normal. If you want to see him again, you can nudge it without making it heavy. Something simple, like asking if he wants to grab coffee after work one day. If he’s interested, he’ll meet you halfway.

Just don’t twist yourself up trying to read every signal. Let it be easy, or let it fade. Either way, you’ll be okay.

[Natalie Noah]

I can feel how much you like this man the excitement, the chemistry, the way he makes you light up inside. And honestly? It really does sound like there is something there between you two. The way he sought you out, joked with you, made sure you were included… that’s not nothing. That’s a man who enjoys you and feels drawn to your energy. But here’s the truth you deserve to hear: you’ve already made a move. Twice. You gave him the opportunity, you opened the door, and you did it with grace. Now it truly is his turn. Not because of some dating rule, but because you need to see if he’s willing to step forward not just flirt in convenient moments, but take actual initiative.

Right now the best thing you can do is exactly what April said keep showing interest, but let him chase. Flirt with warmth, not pressure. Let him feel the space where he has to decide whether he wants to step into something real with you. Sometimes men stay in a comfortable “flirty-friend zone” because it’s safe; they get closeness without the vulnerability of asking you out. But when you shift your energy less friendly, more feminine and inviting it becomes clearer that if he wants access to you, it has to move forward. And if he doesn’t take the step? That tells you everything you need to know. You don’t ever have to chase a man who truly wants you, he’ll make it known.

[Member]

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