Exegesis:

makarioi hoi douloi ekeinoi … (38) … makarioi eisin ekeinoi ‘blessed those servants … blessed are those.’ makarioi and ekeinoi are emphatic by virtue of their position both at the beginning and the end of vv. 37f and mark the content of both verses as belonging together.

hous elthōn ho kurios heurēsei grēgorountas ‘whom the master when he comes will find awake.’ ho kurios here takes up ton kurion in v. 36.

grēgoreō (also v. 39) ‘to be awake,’ ‘to stay awake.’

amēn legō humin ‘truly I say to you,’ cf. on 3.8 and 4.24.

perizōsetai ‘he will gird himself,’ cf. on v. 35. Here perizōnnumi is used in the middle voice with reflexive meaning.

anaklinei autous ‘he will make them sit, or, lie down at the table,’ cf. on 2.7.

kai parelthōn diakonēsei autois ‘and after coming he will serve them, or, wait on them.’ parelthōn is best understood as referring to coming to the place where the servants are reclining. For diakoneō cf. on 4.39.

(V. 38) kan en tē deutera kan en tē tritē phulakē elthē ‘and whether he comes in the second or even in the third watch….’ kan … kan lit. ‘and if … and if’ is best understood as ‘whether … or even’; it does not refer to two contrasting possibilities, but rather has ascensive meaning, since the time of the second night watch is already very late. For phulakē cf. on 2.8. The reference is here probably to the Jewish and Greek division in three.

kai heurē houtōs ‘and finds (them) so,’ with autous understood. houtōs means grēgorountas.

Translation:

If the structure of the first sentence is too heavy one may shift to, ‘if he/the master comes and finds those (or, his) servants awake, blessed are they.’

For blessed, or ‘happy,’ see 1.45.

Servant. The Revised Standard Version uses this term for Gr. pais, lit. ‘child,’ ‘boy’ (1.54, 69; 7.7; 15.26), oiketēs, lit. ‘domestic (slave)’ (16.13), doulos, lit. ‘slave’ (2.29; 12.37-47; 14.17-23; 15.22; 17.7-10; 19.13-22; 20.10f), and in the expressions “menservants and maidservants” (paidas kai paidiskas, 12.45), “hired servants” (misthioi, 15.17, 19). Gr. doulos is rendered “slave” in two passages (7.2-10; 22.50); diakonos, the word most closely corresponding to ‘servant,’ does not occur in Luke. Juridically speaking each of these ‘servants,’ with exception of the misthioi, probably was a ‘slave’ in that his person and work were at the disposal of another, i.e. his owner or master, but in most New Testament passages this juridical aspect does not predominate. Socially speaking the slave played an important role in New Testament times; he did all and any kind of work, from labour on the field and menial jobs in- and outside the house to the task of manager or agent (cf. 12.42f; 19.13ff; 20.10ff) and he had a recognized social status; possession of slaves was not subject to moral reprobation. Accordingly Gr. doulos did not have the bad connotation that ‘slave’ has in languages reflecting other norms. In such languages the term for ‘slave’ (for which see above 7.2) can better be reserved for those passages where the juridical aspect comes to the fore; in other passages a word for ‘servant’ (i.e. one who exerts himself for the benefit of another, i.e. his employer), will be preferable, e.g. ‘one who is sent here and there’ (Navajo), ‘one who does errands’ (Copainalá Zoque, for Mk. 9.35), ‘one-who-works-for-you’ (Ekari), ‘helper’ (Highland Puebla Nahuatl). In some languages one may have to choose between distinctive terms according to the task the servant has to do, e.g. ‘labourer,’ ‘domestic servant,’ etc.

When he comes, i.e. comes home/returns.

The rendering of he will gird himself may be basically the same as in v. 35a, but in some cases a distinction must be made, e.g. in Balinese, where one who is waiting upon persons at a meal would not wear a tucked-in sarong (which is informal dress) but ‘wraps-himself-in a saput (i.e. a garment worn over the sarong, covering the body from the breast to the knees)’; similarly in Batak Toba, ‘puts-on his-ceremonial-dress.’

Have them sit at table, or “make them take their places at table” (An American Translation), ‘cause them to sit down to eat,’ ‘seat them at the place of food’ (Zarma), ‘invites them to take the meal,’ ‘tell them to come and sit to eat’ (Ekari); and see 5.29.

Serve them, here in the sense of, ‘wait upon them (at the meal),’ ‘serve the meal, or, the food to them.’ The verb used often has to differ from the one occurring in the rendering of “servant”, see above.

(V. 38) In the second watch, or in the third, or, “even if it is the middle of the night or before dawn” (New English Bible, similarly Kele), “as late as midnight or even later” (Good News Translation), ‘before or after noon of night’ (Kituba, similarly Kekchi).

Quoted with permission from Reiling, J. and Swellengrebel, J.L. A Handbook on the Gospel of Luke. (UBS Handbook Series). New York: UBS, 1971. For this and other handbooks for translators see here . Make sure to also consult the Handbook on the Gospel of Mark for parallel or similar verses.