Cannot Keep a Girlfriend Very Long

People write in to ASK MIDLIFE BACHELOR with questions.  An index of all Q&As is located on the ASK MIDLIFE BACHELOR INDEX page. Email your question in complete confidence to [email protected].

DEAR MIDLIFEBACHELOR :  I am 36 years old, and I never seem to have a girlfriend for very long.  What can I do to turn this situation around?  Brian K, age 36, Portland, OR.

MLB ANSWER:  You have not really given us enough information.  It sounds like you can GET a date, but getting a second date is problematic. It might be your personality – how you conduct yourself around women.  Or it could be that you are going after the wrong type of woman.  Or both.   I suggest that you check out the Dating Advice section of this site, and pay particular attention to The Midlife Bachelor Personal Makeover for starters, as you might have some appearance and/or (more likely) personality challenges.  After those potential issues are addressed, you will need a strategy – so be sure to read Develop a Strategy for Midlife Bachelor Success.

DEAR MIDLIFEBACHELOR :  I’ve been dating this woman for about a year, and she is a pretty good girl.  Nice looking, professional, and level-headed in many respects.  But she is extremely jealous and always accuses me of looking at some girl, or of talking with one of my ex’s, etc.  How can I get her to stop being jealous?  She would be PERFECT if only she were not so jealous.   George R., age 46, Phoenix, AZ

  You did not state how old the woman you are dating is, but assuming she is at least age 30, it is a very safe bet that she will ALWAYS be the jealous type.   You have two choices – cater to her jealousy and deal with it as-is, or cut her loose so she can become someone else’s problem.   Jealousy is a fundamental personality type (see Types of Women – Jealous), and is commonly paired up with attributes such as Showgirl (see Types of Women – Showgirl) and/or High Maintenance (see Types of Women – High Maintenance) and/or Psycho (see Types of Women – Psycho).  If you decide to just deal with her jealous nature (and her other issues) by sucking it up, then recognize that it will likely get worse over time.   The key question you have to ask yourself – is she really worth it?   If you do think she is worth it, then ask yourself why you think so.  It might be that you are afraid to be single (see Rebound – Does fear of being single drive your behavior?).  You might need to reconsider your entire strategy – in which case I would recommend you read Develop a Strategy for Midlife Bachelor Success.

DEAR MIDLIFEBACHELOR :  On Friday night, I will be going out with a woman who I’ve wanted to date FOREVER.  We’ve gone out twice recently, and the dates were more on the “friend” side of things – in other words, there was no kissing or anything at any point.  I really like this woman, but I don’t want to blow it by making a move on her too soon.  She is really conservative.  Do you have any suggestions about how I should conduct myself on this date?  Jim B, age 40, San Diego, CA

  I suggest you keep in mind the Golden Rule of Bachelorhood, and that is ALWAYS GO FOR IT.  You have nothing to lose by trying to give her a major kiss.  If you don’t go for it, then she will think you are only interested in friendship.  If you do try to make out with her, and she says “no” – then you will know that you tried, and that she is the one who wants to be “just friends”.   You should probably read the Step 2 Conquer the Basics and Start Dating section of Develop a Strategy for Midlife Bachelor Success – and pay particular attention to the Developmental Dating subsection.   In that subsection, you should read and re-read the Watch for Signs page, as well as The Look, the Goodnight Kiss, The Three Date Rule, and Time to Dump Her pages.

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About the Author

Midlife Bachelor chronicles lifestyle, dating, and relationship experiences and advice to avoid a midlife crisis. Readers like you are often beyond young adulthood in their 30’s, 40’s, and 50’s that want to understand how dating, sex, relationships, and love fit in with our lifestyles.