2:1 You know [by personal experience], brothers [those converted under Paul’s ministry in Thessalonica], that our visit [brief in duration but effective in its impact (Acts 17:1-10)] to you was not a failure [hollow, empty, vain, ineffective, worthless; refers to Paul’s preaching; visit might have appeared to be a failure because they had to secretly leave town at night (Acts 17:10); on the contrary Paul’s preaching was full of power; the Thessalonians’ response to the gospel was proof that Paul’s ministry in Thessalonica was not a failure].
2:2 We had previously suffered [cf. Acts 16:22-23] and been insulted [to abuse or to treat shamefully] in Philippi [cf. Acts 16:11-40], as you know, but with the help [“Divine work can only be accomplished in dependence upon Divine strength.” (Watchman Nee)] of our God [Paul relied on God’s help and strength] we dared to tell you [to speak freely with boldness and courage] his gospel [the same message that had triggered opposition in Philippi; see also 2:8,9] in spite of strong opposition [conflict; Paul willing to suffer for what he believed (evidence of his sincerity and genuine motives)].
2:3 [note three ways in which Paul and his companions were not preaching; these reflect the charges that had been made against Paul and his team by their enemies] For the appeal [exhortation, encouragement] we make  does not spring from error or  impure motives [such as ambition, greed, or pride],  nor are we trying to trick you.
2:4 On the contrary [Paul refuted the accusations of his enemies], we speak [and will continue to speak] as men approved [to approve after examination or testing; deemed fit; endorsed by God] by God to be [purpose or goal of the approval] entrusted with the gospel. We are not trying to please men [characteristic of false teachers; cf. Gal. 1:10] but God, who tests our hearts [cf. Jer. 17:10].
2:5 You know we never used flattery [flattery for the sake of self-interest; flattery is the indispensable resource of those who try to please men; “It is deception by slick eloquence, the idea being to win over the hearts in order to exploit them.” (Lightfoot)], nor did we put on a mask [did not play a theatrical role before the Thessalonians] to cover up [cloak, pretense] greed [selfishness; desire to get more at the expense of others]—God is our witness.
2:6 We were not looking for praise [compliments about their preaching or their hard work] from men, not from you or anyone else [they sought approval from God alone]. As apostles [used in broader sense of “missionaries” or those commissioned and sent out by church (cf. Acts 13:4); Paul and Silas (and possibly Timothy)] of Christ we could have been a burden [Paul practiced his trade to not be a burden to the Thessalonians; see 2:9; (cf. 2 Thess. 3:7-10)] to you [by making demands and expecting monetary help],
2:7 but [note characteristic of Paul’s ministry] we were gentle among you, like a mother [willing to undertake any kind of duty and go to any trouble or effort] caring for [to nourish, to cherish] her little children.
2:8 We loved you [to long for someone] so much that we were delighted to share with you not only the gospel of God [see also 2:2,9] but our lives as well [Paul and his companions held back nothing in their ministry; this involved sacrifice and personal involvement], because you had become so dear to us.
2:9 Surely you remember, brothers, our toil [arduous work; same word used for “labor” in 1:3] and hardship [indicates that there were external factors that made the labor more exhausting]; we worked night and day [refers to long hours] in order not to be a burden [to place a weight on someone; to make demands; Paul was a tentmaker (Acts 18:3); no one could accuse Paul of preaching for monetary profit; Paul’s labor set him apart from false teachers who were a financial burden to their hearers] to anyone while we preached the gospel of God [see also 2:2,8] to you.
2:10 You are witnesses, and so is God, of how holy [describes our duty toward God; set apart for God’s service], righteous [uprightness in dealing with others] and blameless [without reproach] we were [Paul and Silas preached through their words and their lives; they set a consistent example] among you who believed.
2:11 For you know that we dealt with each [they had a personal relationship with each believer in Thessalonica] of you as a father [compare v. 7 where Paul and Silas were like a “mother”] deals with [in matters of teaching and raising children] his own children,
2:12 encouraging [Gr. paraklesis: to come alongside with helpful instruction and insight], comforting [Gr. paramytheomai: to come alongside with sympathy and concern] and urging [testifying; strong discipline] you to live lives worthy of God [to live consistently with God’s commands and character], who calls you into his kingdom [refers to the reign of God in the hearts of believers] and glory.
2:13 And we [Paul, Silas, and Timothy] also thank God continually [without ceasing; expressed ongoing nature of Paul’s gratitude] because [introduces reasons for Paul’s gratitude], when you received [Gr. (paralambano): “to receive alongside or to take to oneself;” denotes an act of objective, outward receiving] the word of God [the gospel message verbally proclaimed], which you heard from us [the messengers], [note how the Thessalonians received the message] you accepted [Gr. (dechomai): “to welcome with approval” (and to act on God’s word by receiving Christ by faith); denotes a subjective reception] it not as the word of men [the message was not merely human ideas; cf. Gal. 1:11-12], but as it actually [really] is, the word of God [divine origin of the gospel], which [the word of God] is at work [only God’s word has the power to transform, guide, and cleanse people’s lives; continues to work (an ongoing process); cf. 2 Tim. 3:15-17] in you who believe [emphasizes the continuing faith of the Thessalonians; cf. Lk. 8:11,15; Heb. 4:12].
2:14 For you, brothers, became [indicates what happened to them] imitators [in the way they faced persecution; Thessalonian believers did not abandon their faith when facing persecution] of God’s [gives theological identity to the word “churches”] churches [multiple congregations] in Judea [first churches to be founded outside Jerusalem; endured persecution faithfully; Thessalonians were not alone in enduring persecution], which are in Christ Jesus: You [Gentile believers at Thessalonica] suffered [cf. Jn. 15:18; 2 Tim. 3:12] from your own countrymen [unbelieving Jews and unconverted Gentiles in Thessalonica; cf. Acts 17:5; read Paul’s testimony in 2 Cor. 11:26] the same things [persecution] those [Jewish Christians of Judea] churches suffered from the Jews [Paul himself had once persecuted “those churches” (Acts 9:1)],
2:15 [note three charges against the (unbelieving) Jews]  who [specifically: unbelieving Jews, especially those engaged in the persecutions cited in 2:14; cf. Matt. 27:25] killed [even though Romans did the actual crucifying] the Lord [title denotes Jesus’ divine nature] Jesus [name denotes Jesus’ human nature] and [before killing Jesus] the prophets [cf. Acts 7:52; Matt. 23:29-37] and  also drove us [Paul, Silas, Timothy] out [cf. Acts 17:10,13; Paul often had to contend with Jewish opposition].  They [those whom God intended to be a light to the nations (Isa. 49:6)] displease [continual or habitual attitude; they do not make it their aim to please God] God and are hostile to all men [all humanity]
2:16 in their effort to keep us from [to hinder, to prevent (continual action); indicates how “they displease God” (2:15)] speaking [the gospel] to the Gentiles so that [the goal of Paul’s preaching to the Gentiles] they may be saved [cf. Acts 22:21]. In this way they always [throughout their history the Jews had killed God’s prophets (cf. Matt. 23:29,31,34-35,37) and by so doing were filling up the cup of their sin; in killing Christ and driving out His apostles, they filled up the cup of their sin to the limit] heap up [to fill up] their sins [plural: indicated many separate acts of hostility to the gospel] to the limit [to the full]. The wrath [“As the cup of the sin had been gradually filling, so had the measures of the divine wrath.” (Ellicott)] of God has come upon them at last [fully or finally].
2:17 But, brothers [an affectionate expression of loving concern], when we were torn away [indicates situation (his departure) was forced (cf. Acts 17:4-9); to make an orphan by separation; “we are like children who lost their parents” (Lightfoot)] from you [the new believers] for a short time [not a permanent separation; indicates Paul and Thessalonians expected to reunite] (in person [face; separation was physical only], not in thought [heart: place of affections; out of sight but not out of mind]), out of our intense [strong, blazing] longing [desire; positive zeal] we made every effort [to make haste; eager] to see you.
2:18 For [because] we wanted [to desire] to come to you—certainly I, Paul [indicates personal concern], did, again and again [repeatedly; several times]—but Satan stopped [to cut in, to hinder, to block, to cut a trench; word originally used of breaking up a road to make it impassable; Paul did not indicate methods (perhaps opposition, illness, travel complications, direct attack by Satan) Satan used to prevent his return to Thessalonica; perhaps Paul did not give details perhaps because the Thessalonian believers knew what he was talking about or Timothy explained to the Thessalonian believers what Paul meant] us.
2:19 For what is our hope [points to Paul’s confidence in the Thessalonian believers], our joy [indicates what Paul would feel at seeing them presented to the Lord], or the crown [alludes to wreath of victory awarded to winners in the games (cf. 1 Cor. 9:25)] in which we will glory in the presence of our Lord Jesus when he comes [refers to Christ’s second coming]? Is it not you [rhetorical question; “It is certainly you, isn’t it?”]?
2:20 Indeed [yes], you [emphatic: you alone] are our glory and joy.