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Dating a guy who was engaged before What could potentially be red flags when dating someone who was previously engaged?

4 Answers
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Well, as I fit this category so I feel somewhat qualified to respond. And my response is, there is nothing specifically different you should look for that you shouldn't look for when dating anyone who has been through a break up of significant consequence.

These days living with someone vs. being engaged doesn't really represent a huge difference with the exception you have 'publicly declared' your intentions following societies norms when you have engaged.

I was engaged when I was 23, we had dated and lived together for 2 years at that point and I was going through the motions of natural progression.

The break up was awful and drawn out, but overall I stand today feeling like I dodged a bullet.

  • Determine which side of the fence they were on. Victim or instigator of the separation. Use this information as a pointer to look for personality traits and clues on their behaviours.
  • If you have dated more than once or twice don't feel shy to ask why it didn't work out, if they are willing to talk about it it's a good sign they have a healthy perspective on it. If they talk too much or get upset I'd take this as a red flag.
  • If they have a repeat history of commitment and separation this is a red flag. I fall into this category, while only engaged once I have lived with partners on a few occasions. I'm aware somethings 'up' with it and chalking it down to experience while I sort it out and not moving so fast to commit the past couple of years.
  • How recent was the separation. If it's less than 6months I'd have reservations. I'm not saying walk away, but take it slow and determine there is really a deep connection and not just a rebound or desperation to fill the gap (standard advice).

Overall I'd say don't see it as a too big of an issue, what's important is the outlook and future. We all have some baggage, especially as we get older.
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I don't think there's anything inherently troublesome about someone who has previously been engaged, or even previously married.  Not every relationship is going to last forever, and not every breakup represents a glaring character flaw in someone.  In fact, there's arguably something admirable about someone who realizes they are making a mistake and stops short of marriage, even though that train is difficult/painful to slow down.  Bottom line, I'd say it's a yellow flag--calling for a slow down and investigation--more than a red flag.

Personally, I would be concerned if someone had been engaged multiple times--that perhaps suggests they are impulsive and fall in love easily without thinking about the consequences.  I would also be concerned if someone plainly wasn't over their ex, but that's an issue that's present regardless of engagement.  I'd be concerned if the failed engagement had to do with infidelity, abusive/unstable behavior, or flakiness by the person who ended the relationship, but again, that would be the case even without the prior engagement.  And lastly, I'd be concerned if the prior engagement was something hidden; if I were to discover a prior engagement on my own 6 months into a relationship, for example, I would be much more concerned than if someone voluntarily and frankly disclosed it after a handful of dates.
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If the engagement broke off within the last six months to a year and/or they bring up their ex regularly. If they ever compare you to their ex, then that's even worse. Now the red flag has hit you between the eyes.
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If they make huge decisions quickly like what if thier marriage didn't work out because they rushed into it?