Q&A: What is the best way to approach this situation?

Question by Megan: What is the best way to approach this situation?
So, I’m 21 and the guy is 33. He used to be my manager, but switched areas. While he was my manager, he waved all of my absences so that I wouldn’t get in trouble for them. He would always give me more hours, call me in, etc., and always made small remarks about me/my attitude/etc. Once, when I was upset over my ex, he was really sweet and consoled me and bumped my shoulder, trying to make me laugh. He gave me his number when he was selling his motorbike so that I could look around and try and find someone to sell it to, but ever since he changed areas, we’ve been texting outside of work. He initiated the first text after he changed areas when he was at the airport going on his vacation. Since then, I’ve mostly initiated the text conversations. Recently, about a few months ago, I broke up with my ex and ever since he (the manager) found out, he’s texted me more frequently. He didn’t know that I was single until I was texting him, saying how cold I was, and he said, “Don’t you have anyone to cuddle?” I told him, no, I’ve been single for awhile, so I don’t have anyone. The next day, we were texting for a lot longer than usual. And then, recently, I texted him saying my plans got cancelled and I was bored and he asked who I had plans with, “A boyfriend ;)” and when I said no, he went, “A romantic friend, then?” and I said no to that, too. Also, he keeps bringing up these movies he wants to see, one of them he knew I would see, and I suggested we go see it and told him to tell me when he wanted to go since he’s more busy and he said that sounded good.

But he said he’s not interested in anyone from work and also that he has his guard up against women right now because he’s scarred from his last relationship. Yet he acts like he’s interested in something more.

Just tonight, he was walking through my department aimlessly and I asked him what he was doing. He had just gotten there, but he said, “I was just getting away from the office. What are you doing?” so I told him and then he followed me and we were talking for awhile, some of it was personal and then it turned to work, but he was asking me when I was going to quit this place. I told him hopefully soon.

So, it almost sounds like he doesn’t want to make any moves because he’s a manager and employees aren’t allowed to see managers, but at the same time, he’s making it out that he doesn’t want to see anyone. My coworker thinks that he’s definitely into me and all my other coworkers used to joke about how we would make a cute couple.

What should I do with this situation?
It’s not that I’m desperate and it’s not that big of an age gap. I have other guys that are interested in me and I’ve tried going out w/them, but at the end of the day, I end up wanting to talk to him. I like him a lot, which is the biggest problem. We’ve known each other for a year, but have only not been working together for a couple months.

Best answer:

Answer by Benjamin
Forget it, he was in 6th grade when you were born, I’ve never seen anyone this desperate

If he’s 23 your 21 then you made a typo
After a hard day, ask him if he wants a drink, don’t get too close, and start a relationship from there

PS it’s best to ignore me since I’m way younger than both of you

Know better? Leave your own answer in the comments!

5 thoughts on “Q&A: What is the best way to approach this situation?”

  1. well no shit the dude likes you. but i’d find someone more of my own age. awkward if you get married and hes retiring and you still gotta work for another 12 years.

  2. Like you said your in the same boat as me lol It does seem as if he’s interested but the whole manager/employee thing is bothering him. I mean why would he ask you when your quitting ya know? Also yes okay he’s been hurt but we’ve all been hurt before he has to move on from it eventually. If you want go out with him see if he wants to grab a drink after work and read his body language and see what he does. Or do what I will do just ask him straight up but keep it professional. That way you will know and you can either move on or try something with him. Because trust me not knowing will drive you crazy to the point where you have to be straightforward and just ask him about it. Good luck hun!

  3. girl, don’t listen to that jerk.

    You’ve been through a lot already.

    All I can say now is… Follow your heart. Do you love him? If you do. Just tell him.

    in fact, AGE. HEIGHT don’t matter. Please don’t judge by the book cover. You see, some 40 year old white guys still get some 20, 30 year old asian wifes. lol
    Those asian wives are there for money. But….

    you need to love him for real. Don’t hurt his feelings. He and you seem to be a great couple.

  4. You need to meet up with him outside of work where you can both talk. He obviously likes you but you need to figure out where this could be headed. If he holds back and just acts casual then you need to forget him and move on. I find it creepy when guys in their 30s talk to younger girls..Especially because Im friends with older guys and its all about sleeping with a younger girl..So be careful that hes not just trying to play games and sleep with you. I mean getting you to quit your job to have a relationship is one thing but dont do all of that if all he plans to do is hookup with you. After all, he did say he was scarred from a previous relationship which puts up a red flag. He already warned you that he may not want to be serious with anyone. I say see what his intentions are but hold back and keep your distance a little you know.

  5. i think age gap is not a problem but it depends on you if you like him so much and you think he is the one go ahead i think you should know him very well first and see if he really likes you or not

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