While many Hollywood relationships seems rife with turmoil, such as cheating scandals, drug addictions and money issues, there are a few cases where there are extraordinarily large suitcases, or trunks of baggage, that shadow the celebrity around. Dating these types, in Hollywood or real life, can be especially difficult.

Michelle Williams is a prime example of this. She’s not only a young widow (of sorts, as her and Heath Ledger were no longer together at the time of his death) but also has a young child, Matilda Ledger, with her late suitor. In addition, Williams has faced the career challenge of growing out of her teenybopper role as a star on Dawson’s Creek as well as most recently, being a victim of Hurricane Sandy.

Jason Segel seems to be the man to take on the job of new paramour in Williams’ life and has experienced tragedy right along with her. Their shared warehouse apartment in Brooklyn was flooded by the superstorm Sandy that was not remotely deterred by sandbags or breakwater. Their destroyed brownstone is another notch on the belt of Williams’ all-at-once tragic and blessed young life, but Segel doesn’t seem to mind; he’s been willing to take whatever storm life throws their way.

Here are a few tips on weathering the dating storm of seeing a person with a freckled past:

1.) Understand Erratic or Intense Emotions May Erupt-Try to be understanding, sensitive and supportive, even if grief or sadness seem to come out of nowhere.

2.) Don’t Be Pushy-Let your new love interest come around on his/her own time. Don’t make dating demands or have high expectations.

3.) Don’t Compensate-Don’t try to replicate or duplicate a deceased loved one or even expect to heal old scars. The person you’re dating needs a fresh start, not old reminders.

4.) Leave it Alone-Don’t drudge up the past; just to try and help them “get over it” or move on. Let the relationship happen at a natural pace and don’t force anything.

5.) Allow Reminiscence Time-If your partner wants to talk about the past or cry, don’t feel threatened or insecure. Let them have their time to vent and also discuss their past, even if it’s with rose-colored glasses.

6.) Accept It-Their emotional and physical baggage are probably somewhat permanent fixtures in their life, so it’s important to not expect for these things to disappear or become substantially improved.

Amy Spagnola lives in Broomfield, Colorado and never gets tired of coconut frozen yogurt. She seeks style scores wherever she travels—including Iceland, Egypt, Russia and Venezuela. She holds a Master’s degree in journalism and loves playing Lois Lane when she’s not in yoga class or showing off her ping pong skills. See more of Amy’s writing at: www.amyspagnola.com