How do I ask him out I don't want to miss my chance AGAIN?

I'm a 26 year old female. I'm still working on being assertive and going after what I want, especially with men. I've significantly improved over the last couple years. However, I missed my chance with a guy I really like, who is EXACTLY what I'm looking for.

I recently took a job at a school and a guy in food service was really attractive and sweet. We had a few promising interactions and I'm confident that we both like each other. He recently took a new job and I was hoping he would ask me out before the semester ended or at least ask for my contacts. But he didn't. He seems so outgoing and comfortable with everyone else but me. :/ I've tried to be the more assertive of the both of us and it helped him warm up to me and we formed a small friendship. But I'm shy too. I haven't got to the point where I was confident enough to add him out. I accidentally told him I would miss him and he kept telling me this wasn't the last time I would see him, that he would be back to visit, somewhat regular and asked was I coming back next year.

I really like him but I won't hold my breath on this one. People get busy. BUT I do hope I will see him again. And since he seemed so sure I thought it is probably a real possibility and I would work on my confidence or what I would say when I saw him next.

I thought about asking for his social media contacts. But then I thought 'what if we weren't alone? What if we were outside passing by? Asking him how his summer was, etc leading up to asking to keep in touch. I really like him and I don't want it to be reduced to a "hi and bye' with neither or us acting.

I'm so new at this and he doesn't seem exactly comfortable with asking me out. I don't want to leave it up to him. Any advice on how a shy person approached another person?

***Just for clarification, I DO NOT have any way of contacting him. I was a big chicken and wanted him to ask. So yes, II'll have to wait until the school year starts up and he comes for a visit.



Most Helpful Guy

  • oh he likes you for sure, I think the reason he didn't ask you out was because he does food services as a job ( delivery guy , I'm assuming). You can just ask him for his contact number. For me , no matter if I like the girl or don't , I'll give her my contact number just cause she asked.

    • You think so? I hope that's not true. He is my age and the cafeteria supervisor and I'm an autistic support aide. I think his job is pretty great. I'm determined to get it next time. LOL I don't want to just see him 'occasionally' .

    • Show All
    • LOL, shyness is a sickness in my opinion. there needs to be a cure

    • Yes I feel like it is sometimes. But I've come a longgggg way. And I'm ready to go after what I want. I was working on it. We were doing good the two chicken**** but school ended LOL I needed more time.

Have an opinion?

What Guys Said 2

  • Snooze you lose

  • i've think i've been in those shoes before. there is an 'i' in chickenshit. just do it next time you see him or both of you are going to regret it.

    • Yeah I regret not asking him directly that day. I don't understand I really thought telling him that I would miss him would prompt him to ask me.

      I guess I should have been more clear instead thinking he knew what I was thinking.

    • i know how you feel. maybe he was caught off guard and wasn't quick enough on his feet to reply how he wanted to as well.. don't worry, you only have like what 9 weeks to go?

    • Yeah and plus who knows how long it will take him to visit. LOL

      It's not far away , school is back August 25th.

What Girls Said 2

  • just ask him directly

  • I'm sorry but if a guy wants to date you you won't have to do all that. Perhaps he has his heart set on another woman. From my experience any guy that I had to pursue had little real interest in me other than just convenience/opportunity

    • I'm confident that he liked me. His eyes got big when he saw me. He would jump up and get me anything I'd ask for and was very nervous and fidgety around me for weeks until I started small talking him. He became comfortable and initiated after that. He asked me was I going to be there next year. I really think he is shy. However if he does have a girlfriend I'll settle for friends. He seems like something special.

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