Unsure if this is appropriate, or how to deal with it exactly.

[lanamarie313]

I'll be honest, I'm 24 and have little experience/understanding of men. So I'll mention that right off the bat. Now, a high school friend of mine (not a close friend, just someone I'd see on occassion) was dating a guy who was almost 10 years older than her, divorced, and had 3 kids WHILE we were in high school. We all tried to discourage her from dating him (he was a decent guy, or so we thought at the time) but still, it seemed like it wouldn't go anywhere given the circumstances. While they were together, my bf at the time and I would double date with this couple - a total of 3 or 4 times.

 

It has now been about 4 months since I broke up with that boyfriend, and about a year since those two also broke up. Me and the friend's ex with 3 kids had no communication outside of those 3-4 dates. About 2 weeks ago, this guy sent me a message on facebook asking how I'm doing. Thinking it was just a friendly message to catch up, I responded. Also, I've lost contact with his ex-gf since high school. Eventually, the conversation carried on into discussions of politics, music, hobbies, movies, etc with him initiating messaging me on almost a daily basis. Sometimes I wouldn't respond for a day or two, and sometimes I would. These conversations were somewhat fun, and I didn't see much harm in them at the time.

 

Eventually, he sent me his phone number and said to text him when I got home, since I mentioned I was heading to the gym to work out. Against my better judgment, I went ahead and texted him. I guess I was just convinced it was a friendly thing, and just conversation. I didn't text or message him for a few days, and then decided to send him a quick text saying hi. We talked for a bit through text, and then I told him I had to go. He asked if I would message him the next day, and since I didn't want to, I lied and told him I'd be going on vacation and would maybe talk to him after the weekend.

 

He responded "Well you can just text me you know, you have my number. You're not going to talk to me all weekend?" That was the first time he made any comment that kind of bothered me. I'm not dating the guy, he hasn't expressed any real interest, and I see no reason I'd be obligated to talk to him at least once over the weekend - we haven't even seen each other in person in over a year, and I don't even talk to my close friends daily! Anyways, I told him I'd contact him if I could, but I did not. After the weekend, I sent him a message (I guess I'm conflicted and feel rude by ignoring him). We chatted for a bit, and I tried to end the conversation after a brief while. He then said "Wait, can I ask you a very personal question?" I was curious, so I said sure. He said "Do you masturbate?" I told him that was a very personal question, and that I refused to answer, and why would he want to know anyways. He said he wasn't being a pervert, but that he thought I was very "complex" and was trying to figure out if I was "sexually repressed" or just not open about my sexuality. I said I didn't see why that would matter, and that I wasn't open to discussing it. He told me he was just asking me because: "I like talking to you. I like you, you're intriguing. I don't mean that in a romantic sense."

 

Mind you, we have never, ever discussed anything of a sexual nature prior to this conversation. I was bothered by this, and sort of ended the conversation.

 

Now, I'm unsure how to handle the situation since it got uncomfortable. I feel awkward just talking to him since he is a friend's ex. I feel doubly awkward since he seems to think that there is some kind of obligation to keep in touch with one another regularly, and triply awkward now that he feels it is OK to ask me personal sexual questions. At the same time, I'm an idiot so I feel very rude just completely ignoring his texts/messages.

 

Is this guy potentially interested and denying it? Is he just a pervert? What is a good, polite way to deal with this? By the way, I'm absolutely not interested in him - he's fun to talk to, but he IS almost 10 years older and has 3 kids, something I absolutely do not want at 24.

[Balzac]

You willingly engaged in an escalating communication scheme but you have no interest? He delved into sexual questioning and you're concerned about rudeness? You're 24, old enough to have some inkling about his interest, you aren't reciprocal so stop communicating w him.

[soccerrprp]

Just stop communicating with him. Done. You have ZERO obligation to continue communicating with someone you say you have no interest in.

[lanamarie313]

You willingly engaged in an escalating communication scheme but you have no interest? He delved into sexual questioning and you're concerned about rudeness? You're 24, old enough to have some inkling about his interest, you aren't reciprocal so stop communicating w him.

 

I'm an idiot, I really do blame myself for that. I genuinely thought, because of prior statements he made, that it was just friendly chit chat. There was NO flirting, no comments, just conversation about music, politics, etc. Rather dry stuff to be honest. I didn't want to read into it, especially since he wasn't being flirty or suggestive in any way. The sexual comment came out of nowhere.

 

I am 24, but haven't really dated much at all, and I'm horrible with guys. This was dumb on my part!

[lanamarie313]

Just stop communicating with him. Done. You have ZERO obligation to continue communicating with someone you say you have no interest in.

 

The thing is, I wouldn't mind talking to the guy here and there as a friend, but I'm not sure what his intentions truly are. If he truly just wants to talk as friends, I am willing to be straight about the fact that I won't discuss sex, but that I don't mind chatting here and there otherwise. We have many similar interests in terms of music and hobbies.

 

If he's interested, I don't want to lead him on or make him think it's mutual, which I don't think I have because I was very straight with him about his questioning being inappropriate. I just don't know because he tells me he has no romantic interest, yet seems to think I should contact him regularly, and thinks it's ok to ask me personal sexual questions?

[Ed the 3rd]

Yeah. Just stop talking to him. He's freaky.

 

I mean who the hell asks that?

[Balzac]

You had background on him. At 28 he was dating a girl 18, hanging out w high schoolers. He likes younger women. He knew you were accepting of his relationship w your friend.

 

You're not interested, cut off communication.

[Emilia]

Is this guy potentially interested and denying it? Is he just a pervert? What is a good, polite way to deal with this? By the way, I'm absolutely not interested in him - he's fun to talk to, but he IS almost 10 years older and has 3 kids, something I absolutely do not want at 24.

He can tell that you are inexperienced and this is an attempt to 'groom' you. You have to be very careful because to him you are giving off a victim vibe. He thinks he can talk to you like this and cross your boundaries because you are too timid to say no. You need to consider the kind of vibe you give off in general.

[soccerrprp]

The thing is, I wouldn't mind talking to the guy here and there as a friend, but I'm not sure what his intentions truly are. If he truly just wants to talk as friends, I am willing to be straight about the fact that I won't discuss sex, but that I don't mind chatting here and there otherwise. We have many similar interests in terms of music and hobbies.

 

If he's interested, I don't want to lead him on or make him think it's mutual, which I don't think I have because I was very straight with him about his questioning being inappropriate. I just don't know because he tells me he has no romantic interest, yet seems to think I should contact him regularly, and thinks it's ok to ask me personal sexual questions?

 

You notice I ended my comment by saying: "...you say you have no interest in...?"

 

I was not absolutely certain that you do not have an interest in him despite your reservations. You protest, but you are reluctant to do something as simple as cutting the communication. You talk about having similar interests, but don't want to lead him on. Well, if you continue with this "uncomfortable" communication, what do you think he'll think? Do you simply like the attention?

 

You need to ask yourself some important questions and go from there. But the answer, if you are not comfortable with him, is simple.

[pyramid]

Omg. This is very creepy. Ignore him and do not feel one shred of guilt about it.