Should She Pursue Former Crush...20 Years Later?

Love, Self

After two decades, is the spark still there? And does his patience indicate respect or disinterest?

Question: I have an unusual situation here...a guy I served with in the military back in my twenties (we are in our mid 40's now), found me on Facebook two years ago (I was married then).  He often sent me texts: jokes, political things, discussions about our kids (we both have teenaged boys, he's divorced).  We discovered that we had crushes on each other back then but were unaware of it. Several months after our initial contact, my husband of sixteen years passed away unexpectedly.  Since his death, this guy has kept contact with me daily via text and phone calls to see how I'm doing.  He is almost always the initiator.  We have become very close and discuss virtually everything.  Lately our discussions have become romantic and he has told me that after a full year has passed after my husband's death, he'd like for us to meet.   He thinks the year is necessary for both me and my kids to be ready for me to begin dating.  My son insists that this guy must want  a relationship with me to work because guys don't wait a year to date a woman they don't care much about, nor do they bother texting girls just to be friends or just to get a piece of ass that's far away (he lives on the other side of the country).  The year is a month away from being completed and I am excited and nervous about finally seeing him.  I am convinced that my son is right, but want another opinion – so what do you think? ...Yvonne

Answer: I have to agree with your son.  Although it is clear that this guy has been interested in you for more than two decades, he is still willing to take things "slowly" out of respect for you, your children, and your late husband.  That shows a tremendous amount of discipline and restraint, even if all he is seeking is a good time.  And though one can never know what exactly is in the heart of another, it does appear that he honestly has deep feelings for you, and at the very least wants to explore the romantic possibilities of a relationship.  While it is certain that he is partially motivated by his desire to finally be intimate with you after waiting all these years, mere sexual desire cannot be his sole motivation.  And given that the only impediment to the two of you "getting physical" (for it seems like you've already shared emotional intimacy) is his desire to allow you to be in a place that is conducive to a relationship built on a solid foundation, one must ascertain that his intent is serious.

Obviously, anything can happen when two people get together after many years of separation.  Anticipation is understandably high, and often the reality is somewhat less satisfying than a long-held fantasy.  However, just as often, the actual contact will exceed expectations, leaving both of you wondering why you waited so long to experience this fulfillment.  And whether you are pleasantly surprised or sadly disappointed, at least you made the effort to pursue happiness, and that is frequently satisfying in its own way.

If this has reached you somewhat "after-the-fact," I do hope that you decided to "go for it" with him, and that things worked out well.  If, however, you have yet to make the leap, I encourage you to do so, for if you don't, I fear you will always wonder what might have been.  Remember: When we look back on our lives, it is usually not the things we did that we regret most, it's the things we didn't do, the words we didn’t say, the path we didn’t take.  Carpe diem!  

© 2012 David M. Matthews.  All rights reserved.

Besides being a relationship coach and author of the controversial book, "Every Man Sees You Naked: An Insider's Guide to How Men Think," David M. Matthews is an Emmy-winning TV Writer/Producer who's worked on some of television's best shows.

For more information on David or to get a copy of his free report on "The Three Things Men Are REALLY Looking For In A Relationship," go to

This article was originally published at . Reprinted with permission from the author.