diff --git a/pandas/_libs/tslibs/conversion.pyx b/pandas/_libs/tslibs/conversion.pyx
index 5a8d0a0ec1670..6dd5b4b2fa798 100644
--- a/pandas/_libs/tslibs/conversion.pyx
+++ b/pandas/_libs/tslibs/conversion.pyx
@@ -265,7 +265,7 @@ cdef convert_to_tsobject(object ts, object tz, object unit,
             ts = <int64_t>ts
         except OverflowError:
             # GH#26651 re-raise as OutOfBoundsDatetime
-            raise OutOfBoundsDatetime(ts)
+            raise OutOfBoundsDatetime(f"Out of bounds nanosecond timestamp {ts}")
         if ts == NPY_NAT:
             obj.value = NPY_NAT
         else:
diff --git a/pandas/tseries/offsets.py b/pandas/tseries/offsets.py
index c1ab752bf9550..e1de9d1bcf832 100644
--- a/pandas/tseries/offsets.py
+++ b/pandas/tseries/offsets.py
@@ -8,7 +8,6 @@
 
 from pandas._libs.tslibs import (
     NaT,
-    OutOfBoundsDatetime,
     Period,
     Timedelta,
     Timestamp,
@@ -16,9 +15,7 @@
     conversion,
     delta_to_nanoseconds,
     frequencies as libfrequencies,
-    normalize_date,
     offsets as liboffsets,
-    timezones,
 )
 from pandas._libs.tslibs.offsets import (
     ApplyTypeError,
@@ -76,73 +73,47 @@
     "DateOffset",
 ]
 
-# convert to/from datetime/timestamp to allow invalid Timestamp ranges to
-# pass thru
-
-
-def as_timestamp(obj):
-    if isinstance(obj, Timestamp):
-        return obj
-    try:
-        return Timestamp(obj)
-    except (OutOfBoundsDatetime):
-        pass
-    return obj
-
 
 def apply_wraps(func):
     @functools.wraps(func)
     def wrapper(self, other):
         if other is NaT:
             return NaT
-        elif isinstance(other, (timedelta, Tick, DateOffset)):
+        elif isinstance(other, (timedelta, DateOffset)):
             # timedelta path
             return func(self, other)
         elif isinstance(other, (np.datetime64, datetime, date)):
-            other = as_timestamp(other)
-
-        tz = getattr(other, "tzinfo", None)
-        nano = getattr(other, "nanosecond", 0)
-
-        try:
-            if self._adjust_dst and isinstance(other, Timestamp):
-                other = other.tz_localize(None)
-
-            result = func(self, other)
-
-            if self._adjust_dst:
-                result = conversion.localize_pydatetime(result, tz)
+            other = Timestamp(other)
+        else:
+            raise TypeError(other)
 
-            result = Timestamp(result)
-            if self.normalize:
-                result = result.normalize()
+        tz = other.tzinfo
+        nano = other.nanosecond
 
-            # nanosecond may be deleted depending on offset process
-            if not self.normalize and nano != 0:
-                if not isinstance(self, Nano) and result.nanosecond != nano:
-                    if result.tz is not None:
-                        # convert to UTC
-                        value = conversion.tz_convert_single(
-                            result.value, timezones.UTC, result.tz
-                        )
-                    else:
-                        value = result.value
-                    result = Timestamp(value + nano)
+        if self._adjust_dst:
+            other = other.tz_localize(None)
 
-            if tz is not None and result.tzinfo is None:
-                result = conversion.localize_pydatetime(result, tz)
+        result = func(self, other)
 
-        except OutOfBoundsDatetime:
-            result = func(self, as_datetime(other))
+        result = Timestamp(result)
+        if self._adjust_dst:
+            result = result.tz_localize(tz)
 
-            if self.normalize:
-                # normalize_date returns normal datetime
-                result = normalize_date(result)
+        if self.normalize:
+            result = result.normalize()
 
-            if tz is not None and result.tzinfo is None:
-                result = conversion.localize_pydatetime(result, tz)
+        # nanosecond may be deleted depending on offset process
+        if not self.normalize and nano != 0:
+            if not isinstance(self, Nano) and result.nanosecond != nano:
+                if result.tz is not None:
+                    # convert to UTC
+                    value = result.tz_localize(None).value
+                else:
+                    value = result.value
+                result = Timestamp(value + nano)
 
-            result = Timestamp(result)
+        if tz is not None and result.tzinfo is None:
+            result = result.tz_localize(tz)
 
         return result
 
@@ -290,7 +261,7 @@ def apply(self, other):
                 # bring tz back from UTC calculation
                 other = conversion.localize_pydatetime(other, tzinfo)
 
-            return as_timestamp(other)
+            return Timestamp(other)
         else:
             return other + timedelta(self.n)
 
@@ -394,7 +365,7 @@ def rollback(self, dt):
         TimeStamp
             Rolled timestamp if not on offset, otherwise unchanged timestamp.
         """
-        dt = as_timestamp(dt)
+        dt = Timestamp(dt)
         if not self.is_on_offset(dt):
             dt = dt - type(self)(1, normalize=self.normalize, **self.kwds)
         return dt
@@ -408,7 +379,7 @@ def rollforward(self, dt):
         TimeStamp
             Rolled timestamp if not on offset, otherwise unchanged timestamp.
         """
-        dt = as_timestamp(dt)
+        dt = Timestamp(dt)
         if not self.is_on_offset(dt):
             dt = dt + type(self)(1, normalize=self.normalize, **self.kwds)
         return dt
@@ -2505,7 +2476,7 @@ def apply(self, other):
                 raise OverflowError
             return result
         elif isinstance(other, (datetime, np.datetime64, date)):
-            return as_timestamp(other) + self
+            return Timestamp(other) + self
 
         if isinstance(other, timedelta):
             return other + self.delta