Hottie Needs to Put Moves on Shy Professional

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 MIDLIFE BACHELOR: I hope you can give me some answers.  I’m beginning to date a 51 year old, never-married, no-kids guy.  I’m late 30’s, divorced, no kids.  He’s a very busy professional (an M.D.) and has worked minimal 60 hour weeks his entire life thus leaving little time for relationships.  He speaks of ex-girlfriends but I don’t know the details other than I know they didn’t like that his work came first.  In the last couple of years, he has realized there is more to life than work and is getting out more.   He comes from a great family … his parents are still married, … spends a lot of time with siblings and nieces and nephews, … goes to church.  He is a genuinely good guy, but very structured and is a real creature of habit.  He’s a private person and has difficulty letting new people into his life.  You have to earn his trust.  I know he’s been burned in the past with relationships, and I can feel how cautious he is.  He also has a lot of money so he may be guarded about my intentions with him.  I’m also younger and attractive so he may be questioning my intentions overall.  I’m the girl people always say can have any guy I want.  How I hate that statement!  I have my own money, don’t need his and honestly, just really like him for the person he is and how I feel when I’m with him.  We have so much in common and it seems like times flies by when are together.  I’m a private person and also have difficulty letting people into my heart, and also chicken to tell him of my real feelings for him for fear of scaring him off.  What do I do?  I feel like we’re in a ‘stalemate’ where we’re both afraid to make a move

– he has not even kissed me yet, and we’ve been out three times.  I’m not 100% sure he knows I like him for more than just friends.  I’m not sure I should be allowing myself to fall deeper for him for fear that he’ll never commit with his history.  I want to protect myself from getting hurt.  I could really like this guy, … I’m afraid I already do.  What advice can you give me?  I appreciate anything you can offer.  Kayla

MIDLIFE BACHELOR ANSWER:  Hi Kayla – thanks for writing in, and wow – thanks for the photo. Photos always help me figure out who I’m dealing with. I’d say that you are easily in the top two percent of good-looking women … f*cking model quality, in my mind … and you are correct, he may be a bit intimidated by your looks. Sometimes people with money are a bit eccentric, and they have to be guarded else they risk substantial losses … plus he may have already experienced emotional and financial pain as a consequence of previous relationships. If he were writing in (instead of you), I’d tell him that it never hurts to be careful.

Kayla – one recurring theme that you will find throughout is the idea or rule that you should ALWAYS GO FOR IT. This means that if there is ever a question about what you should do on a date, or in a certain situation related to dating … that you should simply refer back to the rule. [Men don’t typically press charges – so you should be fine. ha ha] Now this guy (for whatever reason) is shy … so you are going to have to make that first move. You want that first move to be bold, but not over-reaching … so I’d suggest that at the end of your next date, you make the move and give him a really tasty good-night kiss … using lot’s of tongue … and see how he responds. If he gets ‘into it’, then you might find yourself well on your way to a great make out session (which could lead to an even better outcome). If instead, he pushes you away – then there is something amiss … and I don’t think that would have anything to do with you (because you are f*cking hot) … so in that case, don’t take it personally, and proceed to minimally invest in case he is able to turn the corner in the future. If his response is somewhere in the middle, then he’s probably just being a bit overly cautious – and needs some patience on your part … in which case you’ll have to decide if the investment is worth pursuing.

My guess about him is that since he works so much, he is probably overly consumed with his professional responsibilities … plus he is cautious and guarded about his wealth … so he might just need something disruptive like a major kiss from a hot chick to rock his world enough to re-orient his mind where you would like it to be. Let”s face it – the approach I advocate here for you would work for just about any man, right? ;o)

Good luck – please report back with how this effort progresses. Actually, I think it would be great for you consider discussing how this plays out on our Midlife Forum … because I can guarantee you that others are going through something similar, and it would be great to learn from your experiences. So definitely consider joining our Midlife Forum, okay?

Avatar of Greg Smith
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.