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I have narrowed down my search to two firms, both located in the same city. Based on the interviewing process thus far, I have a very difficult (near impossible) choice to make. Since my school is not in the city I am considering, this would require me to make another trip.

Has anybody had either a positive/negative experience partaking in a second look at a firm they have an offer with? Any insight, whether it be personal or secondhand, would help.

Depends on a number of factors. If you truly view the decision as nearly impossible it is so close, I think a second look would be worthwhile. It is a huge decision and meeting more attorneys at both firms and asking more questions would help you make the right decision.

If you're down to two firms and it's a difficult choice, why wouldn't you do second looks? There's no downside, other than taking the time to make the trip (I assume the firms would pay your expenses). And if you don't want to make the trip, at a minimum you can ask the firms to set you up with phone calls with a few associates. Having more information is generally better in making any decision.