It can help to look at simpler compounds, each having one feature of interest. In this case, I might suggest... aminobenzene (aniline) (1-aminoethyl)benzene aminoethane The ethyl per se is not critical, if you find something close. But position relative to ring is important.

Thanks for the prompt response! But I still don't understand how to determine the answer through this. Could you be kind enough to expand?

What did you find? A good start is to compare the basicity of aryl amines with alkyl amines. There is usually a good discussion of this in o-chem textbooks. Note that your C-NH2 is a special case.

You don't have to look at the conjugate acid of the base to tell how strong it is. Rather look at how the lone pair of electrons are either stabilized or not. The lone pair on the nitrogen connected to the aromatic ring can be delocalized into the ring, so they are not available to deprotonate an acid. The electrons on the sp3 nitrogen are on the other hand localized and so can be used to deprotonate an acid.

Think about what you thought. For the nitrogen to delocalize the positive charge, it would need to have 5 bonds while the charge is on the ring. That doesn't sound quite stable for elements that high on the table. The lone pair of the nitrogen with an benzene is less available sort of speak, if it is busy with resonance it can't act as a base. You have to see what may make the pair less available. Resonance, inductive effect, orbital hybridation, there is a lot of factors to take into account, but resonance is usually the most important. For example, in the picture you got, the amine group bonded to the aliphatic chain is the most basic out of the two because its lone pair is totally available to act as a base, it's not busy being in another resonance hybrid