There are multiple approaches to instantiating views from xib files. One common issue is assigning the Class to the wrong thing.
Using your code, make sure you have assigned the class to File's Owner:

Here's a simplified example from your image / code:
DatesView.xib source
<?xml version="1.0" encoding="UTF-8"?>
<document type="com.apple.InterfaceBuilder3.CocoaTouch.XIB" version="3.0" toolsVersion="15505" targetRuntime="iOS.CocoaTouch" propertyAccessControl="none" useAutolayout="YES" useTraitCollections="YES" useSafeAreas="YES" colorMatched="YES">
<device id="retina4_7" orientation="portrait" appearance="light"/>
<dependencies>
<deployment identifier="iOS"/>
<plugIn identifier="com.apple.InterfaceBuilder.IBCocoaTouchPlugin" version="15510"/>
<capability name="Safe area layout guides" minToolsVersion="9.0"/>
<capability name="documents saved in the Xcode 8 format" minToolsVersion="8.0"/>
</dependencies>
<objects>
<placeholder placeholderIdentifier="IBFilesOwner" id="-1" userLabel="File's Owner" customClass="DatesView">
<connections>
<outlet property="contentView" destination="iN0-l3-epB" id="Yhm-Z4-6Rd"/>
<outlet property="fromDateLabel" destination="cfP-lM-bLV" id="QeZ-ly-bag"/>
<outlet property="toDateLabel" destination="WGv-5C-gVM" id="Wl6-DR-OuA"/>
</connections>
</placeholder>
<placeholder placeholderIdentifier="IBFirstResponder" id="-2" customClass="UIResponder"/>
<view contentMode="scaleToFill" id="iN0-l3-epB">
<rect key="frame" x="0.0" y="0.0" width="375" height="76"/>
<autoresizingMask key="autoresizingMask" widthSizable="YES" heightSizable="YES"/>
<subviews>
<label opaque="NO" userInteractionEnabled="NO" contentMode="left" horizontalHuggingPriority="251" verticalHuggingPriority="1000" text="From Label" textAlignment="natural" lineBreakMode="tailTruncation" baselineAdjustment="alignBaselines" adjustsFontSizeToFit="NO" translatesAutoresizingMaskIntoConstraints="NO" id="cfP-lM-bLV">
<rect key="frame" x="8" y="8" width="134" height="33.5"/>
<color key="backgroundColor" red="0.99953407049999998" green="0.98835557699999999" blue="0.47265523669999998" alpha="1" colorSpace="custom" customColorSpace="sRGB"/>
<fontDescription key="fontDescription" type="system" pointSize="28"/>
<nil key="textColor"/>
<nil key="highlightedColor"/>
</label>
<label opaque="NO" userInteractionEnabled="NO" contentMode="left" horizontalHuggingPriority="251" verticalHuggingPriority="251" text="To Label" textAlignment="natural" lineBreakMode="tailTruncation" baselineAdjustment="alignBaselines" adjustsFontSizeToFit="NO" translatesAutoresizingMaskIntoConstraints="NO" id="WGv-5C-gVM">
<rect key="frame" x="266.5" y="8" width="100.5" height="33.5"/>
<color key="backgroundColor" red="0.97305089235305786" green="0.92194973774024858" blue="0.86304229628289908" alpha="1" colorSpace="custom" customColorSpace="displayP3"/>
<fontDescription key="fontDescription" type="system" pointSize="28"/>
<nil key="textColor"/>
<nil key="highlightedColor"/>
</label>
</subviews>
<color key="backgroundColor" red="0.78049301826098361" green="0.95023679298999175" blue="1" alpha="1" colorSpace="custom" customColorSpace="displayP3"/>
<constraints>
<constraint firstItem="vUN-kp-3ea" firstAttribute="bottom" secondItem="cfP-lM-bLV" secondAttribute="bottom" priority="999" constant="8" id="8mH-tY-Xpd"/>
<constraint firstItem="WGv-5C-gVM" firstAttribute="top" secondItem="vUN-kp-3ea" secondAttribute="top" constant="8" id="BMT-uj-nrj"/>
<constraint firstAttribute="trailing" secondItem="WGv-5C-gVM" secondAttribute="trailing" constant="8" id="Dyv-OC-Mej"/>
<constraint firstItem="cfP-lM-bLV" firstAttribute="leading" secondItem="vUN-kp-3ea" secondAttribute="leading" constant="8" id="Yoh-Mn-Epa"/>
<constraint firstItem="cfP-lM-bLV" firstAttribute="top" secondItem="vUN-kp-3ea" secondAttribute="top" constant="8" id="oTg-QC-oRP"/>
</constraints>
<freeformSimulatedSizeMetrics key="simulatedDestinationMetrics"/>
<viewLayoutGuide key="safeArea" id="vUN-kp-3ea"/>
<point key="canvasLocation" x="138.40000000000001" y="330.13493253373315"/>
</view>
</objects>
</document>
DatesView.h
// DatesView.h
// Created by Don Mag on 1/30/20.
#import <UIKit/UIKit.h>
NS_ASSUME_NONNULL_BEGIN
@interface DatesView : UIView
@property (strong, nonatomic) IBOutlet UIView *contentView;
@property (strong, nonatomic) IBOutlet UILabel *fromDateLabel;
@property (strong, nonatomic) IBOutlet UILabel *toDateLabel;
@end
NS_ASSUME_NONNULL_END
DatesView.m
// DatesView.m
// Created by Don Mag on 1/30/20.
#import "DatesView.h"
@implementation DatesView
-(id)initWithCoder:(NSCoder *)aDecoder {
self = [super initWithCoder:aDecoder];
if (self) {
[self initializeSubviews];
}
return self;
}
-(id)initWithFrame:(CGRect)frame {
self = [super initWithFrame:frame];
if (self) {
[self initializeSubviews];
}
return self;
}
-(void)initializeSubviews {
self.backgroundColor = [UIColor clearColor];
NSBundle *bundle = [[[NSBundle mainBundle]loadNibNamed:@"DatesView" owner:self options:nil]firstObject];
[self addSubview:self.contentView];
self.contentView.frame = self.bounds;
}
@end
TestXIBViewController.h
// TestXIBViewController.h
// Created by Don Mag on 1/30/20.
#import <UIKit/UIKit.h>
NS_ASSUME_NONNULL_BEGIN
@interface TestXIBViewController : UIViewController
@end
NS_ASSUME_NONNULL_END
TestXIBViewController.m
// TestXIBViewController.m
// Created by Don Mag on 1/30/20.
#import "TestXIBViewController.h"
#import "DatesView.h"
@interface TestXIBViewController ()
@end
@implementation TestXIBViewController
- (void)viewDidLoad {
[super viewDidLoad];
DatesView *dv = [DatesView new];
dv.fromDateLabel.text = @"12";
dv.toDateLabel.text = @"19";
[self.view addSubview:dv];
dv.translatesAutoresizingMaskIntoConstraints = NO;
UILayoutGuide *g = [self.view safeAreaLayoutGuide];
// constrain Top, Leading, Trailing at 40-pts
// NO Bottom or Height constraint
[NSLayoutConstraint activateConstraints:@[
[dv.topAnchor constraintEqualToAnchor:g.topAnchor constant: 40.0],
[dv.leadingAnchor constraintEqualToAnchor:g.leadingAnchor constant: 40.0],
[dv.trailingAnchor constraintEqualToAnchor:g.trailingAnchor constant: -40.0],
]];
}
@end
Result:
