My Boss Is Giving Me Mixed Signals And I Don’t Know How To Deal With Him

The first day I was introduced to him as the new assistant, he looked at me in a way that wasn’t comfortable at first. It was like I was below his expectation or I didn’t measure up to the standard of the person he wanted as his personal assistant. He showed some kind of uninterested attitude towards me as if he didn’t want to engage me. The HR said, “This is the new assistant. He looked up at my face and then he dropped his gaze. For the rest of the time that I was in his presence, he didn’t look at us again. He was doing something on his computer while talking to us. He said, “Ok. And you think she can handle the job?” The HR responded, “Yes, from the qualification and experience she presented, she can. Unless there’s something else we didn’t get to know.” He said, “Ok, let’s see.”

He didn’t ask for my name and didn’t say a word to me. On our way out, I asked the HR, “Is he a difficult person?” She answered, “It depends on which side of him he presents to you. He can be very accommodating today and in the next moment become a thorn in your flesh. But he’s not a bad person. If you learn quickly on the job, you’ll be able to figure him out and know how to deal with him.”

The first day was tough. He didn’t talk to me and he didn’t ask me to do anything for him. I knew his schedule and knew where he had to go and the meeting he had to attend but when it got to the time he had to ask questions, he avoided me and spoke to the Administrator directly. For a whole week, it was like that. My spirit left the job. I wasn’t happy. It was like I’d failed in my role even before it started. During my second week, he began to warm up to me. He asked a few questions and asked me to complete some tasks for him. I was eager to impress him, to make him know that I wasn’t a bad choice after all. Slowly, we warmed up to each other and from there, everything was smooth.

I woke up each morning with this strange eagerness to be at work. All of a sudden, I loved my job and wanted to be on it every time. We returned from a meeting one day and all my perceptions about him changed. For the first time, we talked about issues not relating to work. He spoke about his family and two kids. He asked if I was getting married anytime soon and I told him about my fear of marriage. He said, “We all had fear before we went in. Even after you’re married, the fear doesn’t go away. Every now and then new fear comes up and new challenges spring up. It’s all about your mindset.” I loved the conversation and I was happy to know about him from that angle. He told a story of how he met his wife and some of the challenges they were going through as a couple.

He asked the basis of my fear and I told him how my immediate ex treated me. He laughed at me and said, “Guys are like that but some guys can also be very clean. It depends on who you meet and how you handle him.” After the meeting, he drove to a place where I could easily get a car home. A few minutes after I got home, he sent a message asking if I was home. I answered, “Yes, please. I’m home. Thanks for asking.” The following day was a weekend. He texted. He asked about my weekend plan and I told him. He told me he was in the office and he wanted me to do something for him. I asked if I could come over and he told me, “No, don’t worry. I will manage. I should have told you earlier.”

He spoke to me often. He to me I was the only person he felt comfortable talking to because he likes how I listened to him. Over time, he started sharing his marital issues with me. I wasn’t comfortable hearing all that. I felt it was too much information between a boss and a subordinate. He didn’t care about sharing anyway so I always gave him a listening ear. One evening he texted, “If you’re free tonight, can we go out?” In the next few hours, I was sitting next to him in a bar far from town. He said, “Thank you for coming. You’re slowly becoming the best thing that happened to me in a long while.” We talked. I watched him dance and I laughed. He was tipsy but the lucidity in his flow wasn’t lost. The night was far spent. He drove me home and said goodbye.

I started thinking about him differently. “Does he like me as in like me or he likes me as in just like me?” I couldn’t answer that so I left it in the hands of time.

It was a job trip. My job was to arrange the details of his travel and leave the rest in his hands. But he told me, “You’re going with me so don’t make it look like I’m travelling alone.” I was like, “Seriously?” He answered, “Yeah, I’ll need you to do your job while there.” We booked different hotel rooms but we spent most of the night outside and slept very late.

During our last night there, he walked me to my hotel door and said good night. I entered and locked my door but he didn’t walk away. When I looked at the tiny space beneath the door, I could see his feet and his shadow on the floor. I was looking at him through that space, waiting for him to leave or come in but he stood there for a long while before slowly walking away. He texted me from his room. He asked me, “Do I make you uncomfortable in any way?” I answered, “No, you don’t.” He said, “Good night.”

Now, I’m thinking about him differently. To be honest with myself, I’ve fallen in love with him and waiting for the day he would propose. He gets closer to proposing and then he would back out. We travelled again one time. It wasn’t even work-related. I thought he was going to propose on that trip but he didn’t do it. We spent the weekend in two separate rooms while we talked across from our rooms. It got confusing and I’d wanted to ask him why he was doing all that. From everything he tells me, he’s not happy in his marriage. He told me his happiness is his kids and not the marriage itself because everything is not the same. He wants me and I know it. I want him too regardless of the fact that he’s married. He deserves some happiness and if he thinks he can get that happiness from me, then why not?.

There’s no help I ask from him that he doesn’t give me. When my dad was sick and I needed to be with him, he gave me one week off. It was unofficial. It wasn’t part of my leave. When he called and I told him my dad wasn’t getting better, he sent me money. When I returned from the trip, he sent me money saying, “I know you’ve spent everything on the old boy. Use this for your upkeep until the month ends.” The money he gave me was twice my salary. He’s a good person, to be honest. It’s the reason I don’t mind being with him.


I told myself, “A month from today if he doesn’t make a move, I will ask him if he likes me and he’s finding it hard to say it. If he answers yes, I will accept the proposal he hasn’t been able to say. Everything now is one-sided. He gives me without asking for anything. I feel bad for him. There should be something I have to do for him. Currently, what we are doesn’t affect our work in any way. When we are in the office, we play it professionally. After work, we play a friendly match. My only confusion is the fact that he hasn’t said anything to me. My question is, can a man do all these for you and still not want anything? Is it possible?.

I’m twenty-four and I’ve been in a couple of relationships. When I was in school, lectures gave something to take something. I didn’t like them so I always walked out of their snares. This one is different. He’s a great man with good intentions for me but he’s not being straightforward with me. That’s my confusion.