Dead in Bermuda is a survival/management game where you have to maintain a group of survivors on a deserted island after a plane wreck. It's quite straightforward and fun to play, and you can easily acquire nearly all the achievements just for completing the game. However, there's a couple of tricky ones that need a lot of finessing to acquire. I'm hoping this guide helps clear up a few things regarding those achievements.

If you've never played this game before, be aware that there are two general things to keep in mind that will make the experience a lot easier as a whole.

First, you can actually lower the difficulty when you pause the game. This option can be easy to miss, because it doesn't show up in the actual settings menu. It's basically a toggle that you can turn on/off at any time and it will make all the negative effects (such as fatigue, depression, etc) accumulate slower, while making all the positive actions (resting, eating, etc) more effective. For a resource management game, this obviously makes a huge difference.

Second, all of your gathering efforts (scavenging, hunting, fishing, etc) will suffer a penalty the longer you keep playing, meaning less resources/food gained. However, if you just quit to the title screen and resume the game from any checkpoint, the penalty is reset, so I suggest hopping out and back in every 10 or so in-game days. In prolonged sessions, this quick refresh can be the difference of getting 8-16 wood from scavenging compared to getting 4-8 wood.

Romance
Can you feel the love tonight?


Bad Romance
Flirting to obtain something is an old technique.


These two achievements are about Alejandro's two potential love interests: Bethany (Winters) and Julia. To earn these, you'll need to do three things:

1. Maintain a proper relationship score with your love interest & her rival.
2. Wait for the appropriate conversation scenes at the campfire.
3. Ensure certain other characters don't die.

And now, in slightly more detail:

1. Relationship score
Each character has a relationship score with every other character, from -100 to +100. A high score improves efficiency when doing tasks together, but more importantly for the purposes of these achievements, it also allows certain conversations to trigger during nighttime campfire chats. Simply have a high relationship with your intended target (at least combined score 80 for Winters, 60 for Julia) while keeping the relationship score with the other woman below 40 or so.

2. Campfire chat
At the end of every day, a random conversation will happen at the campfire. These conversations are generated from a large pool of 'generic' conversations, as well as ones that can only happen when certain conditions are met. The specific ones you need for this achievement are very likely to trigger once you've met the requirements, so you won't have to worry about waiting 100+ days due to bad RNG until all the other possible conversations have been exhausted (there's a limited number of them). However, you can't trigger the final conversation before day 30 or so (it will likely take longer anyway, in my case it was on day 48).

3. Avoid character death
Some of the achievement-related conversations also include/mention other characters, so you can't go off randomly killing the extra characters just to limit the possible conversation options, as that might lock you out of the achievement during the current playthrough. While you could safely eliminate certain ones, like Illyana, there's no notable benefit. And why would you want to kill a 16-year-old girl, you monster?

And now, in even more detail:

The campfire conversation chain that unlocks the Romance achievement:
1 - Winters and Alejandro politely discuss their previous jobs
2 - Winters and Alejandro discuss tomorrow's chores and flirt
3 - Winters talks about Alejandro's recent injury while flirting
4 - Alice teases Alejandro about his flirting with Winters
5 - Winters and Alejandro discuss their dating life
6 - Alejandro tells Winters that she's special to him
7 - Winters and Alejandro end up holding hands and share a kiss (Achievement GET)

Note that #6 is a point of no return, meaning that once that conversation has triggered, you can no longer get the Bad Romance achievement in the same playthrough (if you were attempting it). Alejandro isn't a cheater, after all.

For Bad Romance, the process is similar, although there are fewer conversations. Notably the point of no return is when Julia invites Alejandro to go skinny dipping with her, meaning you can't get the Romance achievement past that point. But alas, there is no real romance... because Julia was just using her womanly wiles to scope out Alejandro as a potential spy (see the next two achievements). And once you get her campfire monologue where she decides that he's harmless, you'll also get the achievement.

Note that it's still possible to earn Bad Romance even after you've already eliminated the suspected spy. Makes no narrative sense, but hey, at least you won't accidentally lock yourself out of this achievement.

Tango Down!
Fulfill a spy's mission.


Collateral Damage
The real enemy is not always the obvious one.


There's a subplot in the game about Julia being a Russian spy intent on eliminating an enemy agent, who she believes to be one of the three men on the island (other than her husband): Bob, Jacob or Alejandro. To earn these achievements, you need to get certain campfire conversations with Julia. These conversations happen naturally, as long as you don't have too negative of a relationship with any of the three suspects.

1 - Julia has an inner monologue, revealing that she's a spy and she's planning to assassinate either Jacob, Bob or Alejandro.
2 - Julia questions Bob about whether he often travels to foreign countries
3 - Julia questions Jacob about whether he often travels to foreign countries
4 - Julia questions Alejandro about whether he often travels to foreign countries
5 - Julia teases Bob about him spying on her in her bikinis ('can a spy be so dumb?')
6 - Julia probes Jacob about his opinion on the government (Jacob panics internally)

At this point, Julia is ready to suspect either Bob or Jacob. The trigger conditions are:

Jacob: very negative relationship with Julia (combined -50 or lower)
Bob: positive relationship with Julia, plus a previous conversation between Bob and Yuri about Bob's former government work

7 - Julia says she strongly suspects Bob/Jacob of being the spy (once she's suspected either one, you can no longer get the achievement for the other)
8a - Julia says she's sure that Jacob's the one and that she will silence Jacob at the next opportunity (Collateral Damage)
8b - Julia mentions she overheard the conversation between Bob and Yuri and that she will silence Bob at the next opportunity (Tango Down!)

The very next nighttime scene after this one should be the confrontation between Julia and the suspected spy, where she ambushes and kills him.


That's it. Hope it helped!