Does being engaged 3 times sound like a red flag?

[Citizenkirk]

Concerned? Should I be concerned that I as responding too an anonymous person about a relationship senario I know nothing about, other than that one it involves you, Mr or Mrs. anonymous, some guy that got cheated on and was hurt in a relationship previously, and apparently doesn't want to get hurt again, and the person that hurt him.
I don't even know who it is you are concerned about, be it him, his unfaithful ex, you, a concerned 4th. party, or what. The only red flags I see hear, is the possibility of you taking relationship advice from strangers with so little information too go on.
Fortunately for you, I have an example of an engagement senario involving the mother of a good friend of mine who was engaged to her second husband for 10 years. Apparently her first marriage was such a debacle, that she had no intention of experiencing a third. They have been happily married for over two decades now, with no indication of any marital problems other than whatever minor disagreements that every married couple has at one point or another, that have no worse consequences than great makeup sex.
Engagements are a trial run for married life, and a long engagement gives a couple time too get too know each other and experience married life before tying the knot.
As far as any trust issues you may, or may not have with this guy based on his disclosure of this information, I see the fact that he chose too share this personal information with you as an indication that he trusts you, and showing the same trust to him might be a point in your favor.

[Skankhunt]

Yes, it is a red flag. There is something wrong with him, either emotionally (insecurity, fear, anxiety, bad experience etc) or he has a bad intuition and therefore picking the wrong women to marry with.

If he picked the right woman, this would never happened (being cheated on). It's not bad he was engaged 3 time with the wrong women, it just means he should be cautious the next time when it come to picking the right women.

[Xoxocutekitty]

That's a red flag. I get maybe one or even two (like, maybe he was really young and he got "engaged at 17" but then she moved away and then cheating long distance, and then he tried again the second time and then like she cheated 'for no reason'.

Three times suggests that he either:
1) isn't handling relationship problems/ doesn't communicate very well which leads to a desire to look for more aka cheating or
2) has a bad metric for picking partners, where is he finding all of these women that eventually think they can do better than him
3) is possibly a flight risk himself as getting cheated on hurts deep, but can also lead to future self sabotaging behaviors which drive partners away

[CurlyGirl42]

Did he tell you how long he was with these women? One concern would be that he proposes way too early, before he really know the person by heart.
Another is if he can be very jealous. Not letting his girl do a lot of things, like hang out with her friends, and lead for the girl to leave him by cheating.
So just find out a bit more about it and judge yourself if you think he is a good person by getting to know him better.

[TessCasie]

You should inquire more into it.

[Jakeofalltrades93]

maybe a little. at least he was a 3 time widower, that gets suspicious

[bamesjond0069]

Does he got a little dick and suck in bed? I mean that would explain everything.

[Twalli]

Only that he probably proposes earlier than he should.

[JamesRandiDebates]

He must be a slow learner. Hopefully he has learned his lesson by now. All women cheat. Never marry, never cohabitate.

[boxcarjoe]

Was he in the mitary?

[LemiaOfTheCodes]

Depends on the reason why the engagement ended.

[Cherokeehp]

Definitely a red flag.

[Cataphract]

It sounds more like a black flag. Run.

[Anonymous]

Yes, it's a red flag. It's a red flag that women can't be trusted.

[Nahid1707]

I think cheating is wrong though

[douride2]

Sounds odd to me. I would be very concerned.

[AmeerX]

It is not a red flag. It is not his fault

[Nikki1989]

Yes, that would be a worry.

[OddBeMe]

I’m... yeah. Tread carefully.

[gabzz001]

Yes it makes you sound unstable

[Anonymous]

Women just want our money

[Anonymous]

Sounds like a GIANT red flag to me.

[Nazgol]

Yep, definitely it's suspicious

[Anonymous]

Yeah that doesn’t sound good

[likelyOK]

yes I think so

[Anonymous]

He obviously jumps into things super quick.

[thrombis]

Yes I think so

[Iron_Man]

Oh yeah for sure

[Anonymous]

He's lying

[Anonymous]

It’s kinda weird.

[David7825]

Be away from him

[KrakenAttackin]

Major red flag.

[SUMAIREBRAHIM]

Yes it does

[Yourman89]

Run.

[JBVolsFan]

Yea it does

[cb24l]

No not at all