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Pentagram: +1 damage, increases chances of later deals (Rebirth: +20%, Afterbirth: +10%)
Pact: +0.5 damage, +0.7 tears, two soul hearts.
I'd say the Pact. It's basically a free item if you consider the soul hearts, and a quicker tear rate seems better in the long run in my opinion. Soul hearts will also protect any remaining red heart, so overall you'll have more chances to get a deal later (well, you'll be less likely to decrease the chance).
Of course, if you have enough health, take both. :P
(Unless you're playing Antibirth, in which case you won't have any health left.)
Guppys hairball
Or
Fearshot?
Im thinkin fearshot tho i already have guppys paw sooo
If you take Penta first, you end up with one red heart. And it is possible to take a two hearts deal having only one red heart, so you can buy the Pact with your remaining single heart. Not very intuitive I agree, but still, it is possible. :P
Fearshot is very powerful.
If you already took two Guppy items, take the ball (you don't have to hold 3 items at the same time, touching them once is enough). Since you have only one, mmh... Well, items of that set are quite common to be honest. If you're on Devil deal run, it might be worth it. However, if you don't get any other, meh. The hairball is the worst of the set. x)
I'd go for Fear, but I'd be ready to regret that decision later when I see another Guppy item. xD
i died
Kind of risky tanking it, but if you are confident that you can find Guppy Head, Guppy form or any spider/fly summoning item, go ahead,
Dark Bum has low rate on giving blue spiders. It can drop red spiders which can harm you. Just don't be distracted and you should be fine :P