By the end of this, you may need to ask yourself the same question if you haven’t already. First, if he’s over 25 you need to accept the fact that chances are this is a person who has been through a range of emotions, and a range of emotions directed towards other women. Yes, women that he loved and despised and all the ranges of emotions that come with being human when involved romantically.


Relationship baggage is the main one that seems to be of concern. The questions that accompany this issue are ones like, If he wasn’t the one to end it does that mean that he’s “really” over her? Or Is he going to treat me the way he treated his ex (good or bad)? Another good one – He seems sort of damaged by her. Is he really going to be able to become trusting of me or will he just be jaded? If we are talking about an older age then you’re probably not only getting a guy with a history of long-term relationships, passionate flings, rejections and permanent heart ache wounds, you may be getting divorce or at least the letting go of something they thought would be “forever.” Hmmm….familiar?


People spend far too much time on an archeological digging mission when they get to know someone. Although it can be a useful experience to know a person’s relationship history, I think it’s not a good idea to go digging around for it when you are in the early stages of the relationship. Base your impressions off of shared present moment experiences. Notice how you interact with each other doing fun things, or discuss something you’re observing while people watching or something going on in the world at the moment.

If he volunteers the information that’s fine but if you know too much too soon, it can cause you to dismiss them (or give them unnecessary brownie points) too soon based on random facts. At the same time, if you do find out some of his history, try to see both sides of each piece of information you gain. For example, if he is divorced, see that as a positive that he is capable of commitment. Also see it as something that was probably painful in some way. Don’t make any assumptions beyond that about how any aspect of his history is influencing him present day.

Dr. Marie Land LLC | Psychologist Washington DC | Therapist Dupont Circle | Relationships

Unsolicited information he gives you about how past relationships impact him CAN be valuable though. Especially if he is bringing up things that are in the “red flag” category for you such as his confidently admitting his capacity to be selfish and dishonest with women. If there are red flags and ingrained patterns, permission to listen – and abort!


Rather than being intimidated and insecure about the wide range of experiences a person has, be grateful for someone who has richness of experience. Chances are they may have refined their wants and needs along the way and if they are interested in you, how great that you happen to match up with him on multiple levels. Just as you have a larger appreciation for what you want in a relationship, he probably does too. Remember that every past relationship didn’t’ work out for him (or for you for that matter) for a reason. A reason that chances are, still exists. The majority of your impressions of someone you’re dating should be based on present-day experiences. No matter how detailed a picture they may paint you of their past, you’ll never get a full screen color depiction of reality. Rather than refining your intuitive abilities on reading men, base your impressions on just that – impressions of current reality.