v 1 τοτε adv. "At that time" - temporal adverb. Matthew uses this word a number of times in chapters 24 and 25 to express the general idea of something happening around the time of the end of the age.
των ουρανων (ος) gen. "[the kingdom] of heaven" - attributive genitive limiting "kingdom". Of course "the kingdom" is dominion as well as a domain, and "heaven" is a deferential reference to "God", so "kingdom of God" = "the dynamic reign God".
ομοιωθησεται (ομοιοω) fut. pas. "will be like" - compared to, an unusual future tense is used instead of the aorist.
παρθενοις (ος) "virgin" - here a bridesmaid without necessarily being a virgin.
λαβουσαι (λαμβανω) aor. part. "took" - expressing action accompanying the verb "went out."
τας λαμπαδας (ας αδος) "[their] lamps" - possibly the common pottery ship-shaped bowl with a hole at one end for a wick, although a "torch" for outside use is more likely. εις + acc. "to [meet]" - expressing purpose, "in order to …" although with υπαντησις, the sense is usually "coming out to meet"; here of joining with the procession to the groom's house.
του νυμφιου (ος) gen. “the bridegroom" - complement of εις υπαντησιν, usually takes a dative. (There is a variant where και νυμφης, "and the bride" is interpreted by some scholars as the “bridegroom" as messiah and the "bride" as Israel.)
v2 μωραι adj. "foolish" – regardless of its use, this is not a complimentary word. The English idiomatic equivalent is “stupid, dull or sluggish). They were stupid because in spite of all evidence, experience and cultural expectations to the contrary, they were unprepared. And note it is not that they acted stupid, they are stupid. It’s a given. This observation sometimes colors the interpretation of this parable but as I said, their stupidity is a given so is not the point Matthew is saying stupid or not, they didn't have any extra oil or as some commentators noted any oil at all! They took their lamps without oil as if their preparation were the bridegroom’s or the other guest’s problem – think taking a flashlight without batteries! So his problem is their sense of entitlement.
φρονιμοι adj. "wise" – i.e. "practically wise" an idiom, “wise in the ways of the world”.
v3 λαβουσαι (λαμβανω) aor. part. "took [their lamps]" The participle is adverbial, (possibly concessive) "for although the stupid took their lamps, they took no oil with them".
ελειον (ον) "oil" – i.e. olive oil or any oil was used for lighting, especially rancid oil no longer fit for cooking.
v4 αι φρονιμοι adj. "the wise" - "sensible ones” who took oil with their lamps.
τοις αγγειοις (on) "jars" (of extra oil?).
v5 χρονιζοντος (χρονιζω) pres. part. "[the bridegroom] was a delayed " - literally taking his time - the genitive participle is usually translated as a temporal clause; "when the bridegroom was delayed". Possibly causal; because the bridegroom was delayed. Though some commentators make much of the delay, it is probably of small importance. The delay of the bridegroom is not the issue, his coming is imminent regardless, the issue is that is they were not ready, as if he were NEVER coming, and if you aren’t ready you don’t get entry into the wedding banquet! Kingdom parables are meant to be literal.
πασαι adj. "they all" – i.e. the bridesmaids εκαθευδον (εκαθευδω) imperf. "fell asleep" i.e. nodded off. The fact clashes slightly with Matthew's inclusion of the saying "stay awake" in v13 but this is only a problem if you take the parable as an allegory.
v6 μεσης δε νυκτος "midnight" – literally the middle of night is used rather μεσονυκτιον, literally means "midnight" and is not used here. γενονεν (γινομαι) perf. "a shout, loud cry originated, the aoristic perfect tense expressing a stated action, so "in the middle of the night someone shouted" εξερχεσθε (εξερχομαι) pres. imp. "come out!" - "Here is the bridegroom, come out and meet him!".
v7 ηγερθησαν (εγειρω) aor. pas. "they arose” i.e., woke up
εκοσμησαν (κοσμεω) aor. "trimmed [the lamps]" - whatever was necessary to get the lamps ready to burn, including lighting them.
v8 ταις φρονιμοις dat. adj. "to the wise" – a dative of indirect object.
ημιν dat. pro. "[give] us" - [give] to us. Dative of indirect object.
οτι that. expressing cause/reason; explaining why they need some oil, "give us some of your oil because our lamps are σβεννυνται (σβεννυμι) pres. pas. " going out" – (stupid is as stupid does, they ALL left them burn while they were sleeping and so they ran out of oil early). The present tense expresses the thought that the lamps were spluttering from lack of oil, a dramatic detail underlining a sense of urgency.
v9 μηποτε "no" –an emphatic negation so “hell no”, the dramatic narrative agues for the stronger interpretation so this is a subjunctive of emphatic negation, "certainly there is not enough [for both sets of lamps]."
αι φρονιμοι adj. the wise ones λεγουσαι (λεγω) pres. part. "replied" a Semiticism.
ου μη + subj. "[there may] not [be enough]" – a subjunctive of emphatic negation.
υμιν "for us" – a dative of interest, advantage.
τους πωλουντας (πωλεω) pres. part. go to "those who sell oil".
εαυταις dat. ref. pro. " yourselves" - Dative of interest, advantage. Idiom: this is a problem of your own making, solve it yourself.
v10 απερχομενων (απερχομαι) gen. pres. part. "while [they] were on their way" αγορασαι (αγοραζω) aor. inf. "to buy" - adverbial, expressing purpose.
αι ετοιμοι adj. "the virgins who were ready" τους γαμους "the wedding banquet"
v11 υστερον adv. "later" αι λοιπαι adj. "the others" κυριε κυριε "Sir! Sir!" a double vocative to underline the urgency of their plea. λεγουσαι (λεγω) pres. part. "they said" ημιν dat. pro. "[open the door] for us".
v12 δε "but" - adversative - the girls ask to come in but the groom refuses to let them in.
αποκριθεις (αποκρινομαι) aor. pas. part. "he replied", again a Semitic construction.
αμην λεγω υμιν "I tell you the truth" - truly I say to you – a phrase which serves to underline the statement, ουκ οιδα υμας "I don't know you" - an Aramaic turn of phrase which takes the sense "I will have nothing to do with you".
γρηγορειτε ουν, "therefore be on guard." The Noah illustration serves to define the intended sense of this imperative. Idiomatically this means "be prepared." The verb is also used at 24:42 -43 (the watchman is vigilant, not caught out, so we too must “keep watch”). But note all the girls went to sleep, so keeping watch (i.e. staying awake) is not the point. The point is την ημεραν ουδε την ωραν "[you do not know] the day or the hour" – it is the "not yet" of Kingdom Coming, only God knows the moment of it’s fulfilment. So we must be prepared day or night to be alert to its coming, which for us should be no surprise! Delay is about God’s kairos not His chronos. It is not our response, but our preparation at issue.
Preparation and urgency can inform a variety of our practices, from prayer, to worship, to faith formation, to social outreach – in fact the entire life of the church. The virgins know the wedding is going to happen, just not why the bridegroom is delayed. When the wedding is a certainty, why bank on the delay? Focus rather on the inevitable wedding and be prepared for it!