I’m not sure what to do with this friend.I don’t mind having him in my life. But I also don’t see myself interacting with him more than once a month if not less.

He was my professor. I was struggling in the class. But I went to help room a lot and was always asking questions in class. Sometimes I emailed him with problems and he’d always get back to me very fast. In the email, I had always included a sentence like “hope your day is going well” etc. And he’d always reply with how his day was going and ask how I was doing.

After finishing the course, he wanted us to stay in touch. I thought that was cool. Most of the communication stayed with email. I started to get annoyed a bit when he got into the habit of emailing me almost everyday, asking how I was doing. I thought that was too frequent. I pulled back but stayed in touch with him.

One day he suggested us grabbing lunch together. I thought it was fine. During the lunch, I wasn’t feeling all that comfortable. On the one hand, he is always my professor and I may just feel a bit uneasy around professors. On the other hand, I didn’t quite get his jokes or didn’t think they were funny. The conversations didn’t flow. I didn’t like his personality that much that I wanted to know more about him. Unfortunately, we exchanged the phone number.

Then my perspective of him went down hill. He would always bomb me with texts. A lot of times 6 or 7 in a row. Sometimes he’d send me a half dozen in the morning, a half dozen in the afternoon. And A dozen at night. This behavior really annoyed me. I ignored him half of the time.

He’s still single. He mentions a lot times to me that he’s still looking for the one. And that he gets lonely sometimes. I guess he craves companionship a lot of times. He sends me a lot of photos he took, such as sunset, or just random stuff. I don’t mind him sharing his photos with me. But all his photos had been photoshopped and with his signature on. Many times I felt he was seeking compliments from me. To be honest, I’m not too impressed considering they were photoshopped. When he cooks, he sends me photos of every step of his cooking. So when he cooks, I get dozens of messages from him within an hour.

Once we had lunch together. He told me he was seeing this woman but she couldn’t commit to him and he was really bothered. I tried my best to comfort him and asked more of the story. Finally he told me she refused to leave her boyfriend for him. I was shocked to hear that the lady was cheating on her boyfriend to have affairs with him. He kept saying the chemistry was genuine and found many excuses to explain to me that the lady got her feelings confused and he didn’t know how to persuade her to break up. I told him that was cheating and that he should never engage in any physical contact with any woman who has a boyfriend. He said he was desperate and wanted me to comfort him. I had empathy on him in the beginning when I didn’t know they were affaires. Later on I told him to move on but he was texting me many hours throughout the day, looking for my comfort. That was the time when I thought he was so immature and I didn’t know I respected that much to want to still be a friend with him.

I’ve only had lunch with him 3 times. Once the night before the lunch, he texted me that he had a surprise for me tomorrow. I really didn’t appreciate that because why would he tell me to expect a surprise? At the lunch the next day, he gave me a card saying thanks so much for having lunch with him. I thought that was weird. Then he gave me a big container of cookies. He said he made them yesterday and that was his gift to me. I felt weird again because there were more than 20 cookies and I didn’t know why he gave so many to me. Then he handed me the recipe of the cookies and wanted me to read before ordering my lunch. He said he wanted me to keep the recipe. Then he told me to put bread in the cookie container so that the cookies don’t get dry. The lunch was boring. The next few days, he was texting me everyday asking how I was doing with the cookies and if I remembered to put fresh bread in the container. I didn’t think the cookies tasted good and threw them away the day after lunch. I started to ignore his texts on the third day after the lunch.

He has a personal blog. This weekend he encountered a technical problem with his website. He texted he thought he had a problem that I could help him with. Asked if I would mind. And described the problem and that he was very frustrating and said thanks in the text. he sent all these 6 texts at 10pm on Friday. I felt annoyed when I saw them because I didn’t think he was close enough to me to send late night texts. Second he was throwing his problem at me and expected me to be his 24/7 tech support. Although I work in tech, I’m not trained to answer his specific software problems.

I replied him the next day with ways he could find solutions. And told him I couldn’t help me without seeing the problem. Then again a dozen texts saying why he couldn’t find solutions through the ways I suggested and tons of screenshots of the error messages. He’s a premium account user of the software where he hosts his website. Even that the company doesn’t provide customer service over the weekend. I don’t understand why he thought he could require my help over the weekend.

I haven’t replied to him. But I’m seriously thinking if I should do something to prevent myself from being annoyed at him. Not just this time, but once and for all. I don’t know if because he used to be my professor, many times I feel obligated to answer him and provide companionship or compliments or whatever he was seeking. If I had met him as a person, no professor title, I would have no interest in having a friendship with him in the first place. I don’t find his personality attractive. I don’t find connection with him. I find myself forcing the conversations and forcing myself to pay attention to him more than half of the time when he talks.