My Mailman, or, I Desperately Need a Lesson In the Art of Chit Chat

I think me and my mailman like each other. It's clear that we enjoy talking to each other.

Problem is, I often kind of flounder with conversational chit chat and small talk. Today we saw each other and literally there was like 10 seconds (which felt like 10 years, where I didn't know what to say. He doesn't seem to know what to say either. But he is very friendly and is very sweet and nice when ever we see each other.

I felt kind of guilty, because today I ended up just saying "have a good day," after the ten year pause, and headed toward my apartment. Then he walked by my apartment, and started to engage me. He was like, "I'm so glad this is my last stop. I get to go home and relax!" And I just said "Have a good one!" And went inside. Wow. I need help, lol. Someone help me. What do I say to him. I sort of wonder if I didn't WANT to say anything to him. Not because I don't like him. But because I was tired, and I just...thinking of stuff to say in response is actually HARD for me! Also sometimes I'm just not expecting to see him.

I have thought about asking him for coffee before. I'm hesitant though because he might have a girlfriend. Or a boyfriend. Or maybe he's married. Would I have to be the one to ask him out? I do think that might be the case, since he has a government job and he could probably get in trouble for asking people out on his route.

My therapist cautioned me against it. She said "if it didn't work out, would that be awkward? You still have to see him." The thing is though I wouldn't have to all the time. I hardly ever see him now bc I'm busy. He comes to deliver around 11:30. I could easily just avoid him.

What do you guys think? Does it seem like he likes me? Would he not be able to ask me out due to his job? How do I at least get better at the chitty chatty?

Yay, a fun romantic challenge. My advice is keep your relationship to your front stoop and see what develops. In time, if he really wants to go out with you, maybe he would ask for a transfer to a different neighborhood or get a promotion. Who knows what life will bring. Until then, be yourself and don't be pressured into drawing out conversation longer than a few quick remarks or exchanges about the weather. From your description, it does sound like he was fishing to be invited in or meet somewhere after his shift was over. That is a major no-no. If you'd like to find out if he is interested or not, you could invite, or agree to go out with him, and cancel afterwards. That is my advice. Good luck

If he goes home after your stop, i would ask something leading like, "does your wife have lunch waiting for you when you get home?" Think of a few lines like that beforehand, and the right one will be ready when the time is right. Thats how stand up comics practice!

Hey AB. I didn't take it that way, in terms of him comment about going home and relaxing. I took it at face value. He wanted to go home and relax. I just meant it seemed like he was trying to talk to me.

I appreciate you saying not to pressure myself to come up with stuff and that it doesn't have to be long and drawn out! That's validating to me.

I honestly don't think he'd change routes just over someone he'd want to date and get to know.

Just wondering, why do you say not to date him or ask him out? Thanks!

Haha, honestly, sometimes conversation makes me feel like I'm failing an improv class! I was thinking I could come up with some questions to ask him about this and that. I've been totally procrastinating on that. But yeah, it's in the works. And yeah my therapist said the same thing, in terms of finding out if he's with someone. Since it's the holidays, I could ask "what do you do for the holidays? do you have a family? someone special?" I could also just look at his left hand, when he's not wearing gloves, for a ring.

I like unuluna's thought to find out a little more about him. I guess, my first instinct is if asking out a client, co-worker, or in your case a 'regular client' (potentially even more awkward if things went bad), is frowned upon, maybe it isn't such a good idea. I think you're correct in saying that his comment meant what it meant and I may have jumped to conclusions. Still, more personal than 'any' other comment. To me, he does sound interested

My mailman is always very nice and friendly to me. But i think its more just because im a long time resident in this apartment building and many people are transient, being students.

I think finding out more about him is a good idea. I wouldn't let the fact that he is the mailman stop me. I never see my mailman, so avoiding him would be pretty easy.

Yes, find out more about him. A ring is a good example and also using the holidays to ask about family is thoughtful. If you do choose to use holiday festivities to date each other, please be careful. Even the most normal seeming people can turn out to be real creeps

I don't mean to be the only naysayer here, but I'm with your therapist and would also caution against it. How awkward if you DO have to avoid him if it doesn't work out? He comes around your house every single day. I don't think it's a good prospect. Just my honest opinion! I don't mean to burst your bubble, and sorry if I am! Much safer to date those who are not around the workplace, your home, or wherever you frequent.

Thanks Eve! I'll take it into consideration. I'm not really like gaga for him. He's just really nice and cute. What you said is something to think about though.

Well, I just think of my own home as a safe haven for myself. A place where I can completely unwind, be myself, be by myself when I need to and want to be, and away from all that troubles me. Add to that a situation where you may have to avoid someone who comes to your door every day. UGH! Not that it couldn't work out, but just thinking of the worst case scenario. Similar to dating at work... it's a no no for most people for just that reason. Yes, something to think about at least.

Well, although no one can say with certainty the interest level of this guy, based on what you've said, first



"I think me and my mailman like each other. It's clear that we enjoy talking to each other. "

based on that line alone, Idk if it's true that he likes you but clearly you've established some rapport and have had conversations on more than one occasion. So that alone says there is some interest. Whether its that he "likes" likes you or is just enjoying talk... would be hard to say based on that alone but

the fact that when he reached your apartment, he actually engaged you again, kind of says a bit more to me. After you walked away he made an effort to engage you again even if it were just a comment like that he was finished with the day - I think really it was an invitation to conversation again, at the very least. Not only did he engage you again, but he alluded to the idea that his day was ending, possibly implying he has time now... Idk

as for your clumsiness in conversation, I totally understand this and I don't think you're alone in that those silent "10 year" moments are awkward. I know how this goes but I really think a lot of people experience this and you shouldn't be too hard on yourself. It's about feeling like you need to perform well for this person of obvious interest and attraction to us. we want to impress and attract them too and tend to think too hard on what to say and do. Layer that with the type of person who may be socially awkward anyway (me) and it's a killer situation... in a bad way lol. Don't be too hard on yourself because likely if there is mutual attraction, there's likely mutual awkwardness too and he may feel a bit the same too!

I agree with the one to say to keep to your doorstep and/or mailbox, what not.. see where it goes.

I'd say go for it, KnitChick. Try to ask him some questions about his personal life and see how it goes from there. Wish you good luck! Let us know how it goes

Sandman, thanks for the reassurance about being "socially awkward" and the insight into that as well.

Mickey, thank you for the encouragement!

I think I'm going to hold back for now. But it's enjoyable to see a face that is happy to see me, and we do have a nice little rapport. Perhaps it can grow. But I like the idea of not pressuring myself to be anything I'm not. Thinking about it, I'd be pressuring myself if I asked him out.

Update: I'm really glad that I talked about this here. After, I decided to not pursue anything with him and that feels right. He definitely seems to like me. We talked to each other on Christmas eve and the way he was looking at me was creeping me out. Today he even rang my doorbell. I don't usually answer if I'm not expecting anyone. But one time my neighbor locked herself outside of her apt. and rang my doorbell, so I was playing it safe. He said he must have rung it by accident when putting the mail in the slots (It makes sense but I'm not sure he was being truthful). We started chatting and I ended up pulling out of him that he has a girlfriend and two young daughters. He was saying a lot of vague general things about his girlfriend like "its been over for a long time," I suggested relationship counseling and he said "it's way beyond that." Okayyy....... all those things he was saying about her seemed really ****** of him in my opinion and he has a 1 year old daughter with a woman he hates? Ok. It reminded me of the time I was hanging out with a coworker who wanted to hook up with me a few years ago. I found out he had a gf, and he kept saying how awful she was. It was all lies. He was the awful one. Thats another story but it just reminded me.

Anyway, I don't mind talking to him. But if he ever asks me out I will say No. I may pull back a little as well. Not really sure how. I just don't want to give him the impression that I'm into him.

perhaps "I enjoy talking with you casually but I'm not looking for a date".
It sure is awkward sometimes finding out what I want to do in such a situation, and then acting on it.

Hi Knitchick,

I think you should keep this casual. It sounds like he is looking for another relationship, and that relationship could be awkward because (1) He sees you every day as your mailman, and (2) He has a one-year old daughter with another woman. It sounds like you are both attracted to each other, but you are not ready to date him. Be sure to stick to your boundaries regarding a relationship.