The trouble with making an offer...

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...is I don't want to insult the seller, or look like a fool for offering too low, but if my offer is accepted I'm going to worry that I offered too much.

I know this is daft. I should do my research, know the right price, offer what I want to pay, hope it's accepted, and not worry if they would have accepted less, but still... you know? Don't you get that feeling?
 
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The research is key.

If you know the product/market well and are serious about buying.... your offer shouldn't be seen as insulting. If it is then one of you is wrong.
 
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I always do my buying in person so most of the time I can get a feel for what the seller will settle for. I know what you're feeling but it's almost impossible to know what the lowest possible price could have been. Even worse dealing online I would imagine. Usually I'm simply focusing on the watch as that makes it simpler to feel satisfaction with what price I pay.
 
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It's the opposite for me. If I offer a watch for sale and it's snapped up with no haggling, then I know I should have asked for a bit more.
 
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It's the opposite for me. If I offer a watch for sale and it's snapped up with no haggling, then I know I should have asked for a bit more.

or it's priced perfectly...
 
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It is only ever worth what someone else is willing to pay for it.
 
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I never had any problems with offers. I know what I'm buying and what it's worth. A lot of times the seller has a wrong idea. No problem at all, good luck to you. But I've sold my share of watches and I saw the low ballers frequently. It always makes me chuckle. So put in a reasonable offer, dont lowball and do it with respect for someones watch. Then everything will be fine.
Edited:
 
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...is I don't want to insult the seller, or look like a fool for offering too low, but if my offer is accepted I'm going to worry that I offered too much.

I know this is daft. I should do my research, know the right price, offer what I want to pay, hope it's accepted, and not worry if they would have accepted less, but still... you know? Don't you get that feeling?
It may come as a surprise but most people know they won't get what they asked for whatever they are selling!
Put the ball in their court, ask what is their final price, sometimes it's even lower than what you were planning on offering - 60% of the time, it works every time.
 
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Put the ball in their court, ask what is their final price, sometimes it's even lower than what you were planning on offering - 60% of the time, it works every time.
Not with me! 😉
 
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It may come as a surprise but most people know they won't get what they asked for whatever they are selling!
Put the ball in their court, ask what is their final price, sometimes it's even lower than what you were planning on offering - 60% of the time, it works every time.

Only a weak seller answers that question.
 
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Put the ball in their court, ask what is their final price

I would never respond to something like this, and in fact it makes me think poorly of the buyer. If I list an asking price, that is my asking price, I've researched it and I think it's fair. If someone wants to make an offer, that's fine, but I'm not going to reduce my asking price just because someone asks me too. Unless they're a friend. 😀
 
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...is I don't want to insult the seller, or look like a fool for offering too low, but if my offer is accepted I'm going to worry that I offered too much.

I know this is daft. I should do my research, know the right price, offer what I want to pay, hope it's accepted, and not worry if they would have accepted less, but still... you know? Don't you get that feeling?

If the offer you think is fair would insult the seller, then you are probably too far apart to make a deal. Just move on. Either you or the seller may have unrealistic expectations.
 
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Only a weak seller answers that question.
Well, if a seller comes back to you with the asking price (after you asked for their final price) that also give you an indication on how low of an offer you can make.
 
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I’ve had this happen tons of times with “what’s your last price?” “what’s the lowest and final offer?”

In one example I’ve responded with “$6400 is my lowest and absolute final price. I won’t accept a penny less” Then I get “How about $4100 cash?” 🤬
 
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I would never respond to something like this, and in fact it makes me think poorly of the buyer. If I list an asking price, that is my asking price, I've researched it and I think it's fair. If someone wants to make an offer, that's fine, but I'm not going to reduce my asking price just because someone asks me too. Unless they're a friend. 😀

When I ask for the final price I'm not necessarily asking to get a discount, as I said, it also gives you an indication on how to negotiate a price.
You may have done your research but if you priced something and was not able to sell for longer than you wanted to and someone asks for your final price you may reduce just cause an opportunity presented itself.

I’ve had this happen tons of times with “what’s your last price?” “what’s the lowest and final offer?”

In one example I’ve responded with “$6400 is my lowest and absolute final price. I won’t accept a penny less” Then I get “How about $4100 cash?” 🤬

Well, some people are just rude.
 
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My watchmaker called to tell me that one of his clients (a high end family run jewler in town) had gotten a ladies 60's Seawolf in and the customer wanted to sell it. He knows I have a thing for the Seawolf and would love to get one for my lady a his/hers set (we always joke about it).
The jeweler reached out to me and told me that the customer wanted $1.3k for it, I pleasantly declined and said that's ok, thanks for your time. He responded saying that he could pitch her an offer, and asked what it is worth (these aren't in their wheelhouse). I told him I didn't want to insult, but then laid out 2 paragraphs of comps and research so he understood I wasn't trying to insult him (as he is friendly with my watchmaker- I care about that relationship), but was giving him real market value so he understood the customer was not informed of the actual value- I offered $250 (which is top of the market for that kind of ladies watch- but hey, the lady wants it) and would give him a 20% finder's fee for his time.
He thanked me and said he would relay that to the customer. I assumed it was done, but yesterday (2 months after this interaction) he emailed and said she took the $250. I pick the watch up today.
If you just throw a price out to an uneducated seller, it can look like you are just being insulting. If you share your rationale, then they understand you are ernest and can meet you on a more honest playing field.
As Fred said, in person you can read the body language and get a feel for how the seller wants to do business- just the facts and give me a price, or so they want to kibbitz and feel you out before they get to the money part (all part of the foreplay sometimes). It's much tougher online and all depends on what kind of relationship you want.
With eBay and a one off sale with a "make offer button" I will just throw it a low ball sometimes and see if they bite. Second offer will be the real one.
If I am asking for them to take an auction from open to a BiN for me, I will send a 1/2 sentence DM and ask politely with a real value- many times they accept.
 
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If the offer you think is fair would insult the seller, then you are probably too far apart to make a deal. Just move on. Either you or the seller may have unrealistic expectations.

...or someone has not realized that they have included their sentimental attachment into the price
 
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My watchmaker called to tell me that one of his clients (a high end family run jewler in town) had gotten a ladies 60's Seawolf in and the customer wanted to sell it. He knows I have a thing for the Seawolf and would love to get one for my lady a his/hers set (we always joke about it).
The jeweler reached out to me and told me that the customer wanted $1.3k for it, I pleasantly declined and said that's ok, thanks for your time. He responded saying that he could pitch her an offer, and asked what it is worth (these aren't in their wheelhouse). I told him I didn't want to insult, but then laid out 2 paragraphs of comps and research so he understood I wasn't trying to insult him (as he is friendly with my watchmaker- I care about that relationship), but was giving him real market value so he understood the customer was not informed of the actual value- I offered $250 (which is top of the market for that kind of ladies watch- but hey, the lady wants it) and would give him a 20% finder's fee for his time.
He thanked me and said he would relay that to the customer. I assumed it was done, but yesterday (2 months after this interaction) he emailed and said she took the $250. I pick the watch up today.
If you just throw a price out to an uneducated seller, it can look like you are just being insulting. If you share your rationale, then they understand you are ernest and can meet you on a more honest playing field.
As Fred said, in person you can read the body language and get a feel for how the seller wants to do business- just the facts and give me a price, or so they want to kibbitz and feel you out before they get to the money part (all part of the foreplay sometimes). It's much tougher online and all depends on what kind of relationship you want.
With eBay and a one off sale with a "make offer button" I will just throw it a low ball sometimes and see if they bite. Second offer will be the real one.
If I am asking for them to take an auction from open to a BiN for me, I will send a 1/2 sentence DM and ask politely with a real value- many times they accept.

My approach is similar. I make an offer on the lower side of what I think it's worth, it gives them a chance to come back with a counter offer and it still be within what I am willing to pay. If you don't leave yourself room to come up a bit they may take it as you being unreasonable. It also means if they accept you're happy that you got a good price.

If there is a 'make an offer' I always use this formula, a lowish but realistic price, even if it is half the buy it now. Sometimes they accept or haggle, if they don't accept by the time I've come up a bit to my max we are never going to come to an agreement and I just move on, something else will come along. Because I collect Helvetias I know what is out there and sometimes what I'm willing to pay may be less than others as I know it's fairly common or it may be more as I can see something others can't.

Most often I'm surprised when we agree a realistic price way under the initial BIN that's why I always offer what I think is reasonable even if it does seem insulting low as I've got first offer acceptances of 40% of the asking price before.
 
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...or someone has not realized that they have included their sentimental attachment into the price
This happened a lot. Grandpa got this during the war in Switzerland and it's worth a fortune (insert 70's Timex here).
Many times it's just an uneducated seller. They do their market research say- a run of the mil Enicar- and they see Sherpa's going for thousands, so it's the same company, this watch must be worth what those are. Some times a seller can see the err of their ways, and many times, like @Dan S pointed out, they are just too far away from reality- those are the ones you just walk away and thank them for their time.
 
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As an extreme example of buying in person, nothing could have been worse for me than trying to establish the price a seller wants and buying watches in the Philippines. After a couple years there we finally came up with some formats that worked. We used to run ads in all the local papers that we buy watches, and the texts would roll in constantly. If the watch sounded interesting I would have either my wife or a crew member call the seller to ask a few more pertinent questions and set up a meet up. There were 3 standard challenges to this. First was get the seller to actually show the watch, next is the watch genuine, and then finally how much. If we take Rolex for example, easily 8 times out of 10 if we got to the point that the seller met up, which is more challenging than it sounds, the watch was fake. If it was genuine then the 3rd and final challenge was establishing a price. NEVER would a seller blurt out a price, even though they responded to our ad and are selling their watch. The standard answer when asked was "what's your offer?". Absolutely maddening until we honed our technique. We would simply respond "1000 pesos" ($20) with a smile. That usually broke the ice and then with a bit of back and forth they end up giving a price. We always first respond with a ridiculous offer, then some laughter from both parties and more often than not their real price would be reasonable.

We had run into some particularly hard cases where the seller flatly refused to give any idea of a price on their watch, and in those instances we had to work a bit to figure whether they were actually looking to sell the watch at that moment, or merely trying to establish authenticity and idea of it's value. In those instances we would never give any free education, and wouldn't let on much since it might be a novice or competitor sending one of their underlings to learn info on some watch they are considering buying.