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].

I’m a confident, good looking 42 year old male. My longest relationship is a year which was in my mid-twenties. I’ve also dated women for a couple of months with the possibility of a long term relationship, but I’ve always ended it before it got too serious. I’ve also had flings and one night stands. I guess you can call me a commitment phobe, but I’m also very fussy. A part of me wants to settle down and marry. Another part of me is just so used to being a “player”
Lonely Old Man225

and finding it hard to change, because I’m comfortable, and I enjoy dating different women. I’m confused and worried because if I don’t commit to someone, I’ll be very lonely later on in life. The thought of turning 50 and not being in a long-term relationship or married scares me. How will I be perceived? Will people think I’m weird and creepy? Will people question my sexuality? Perhaps I haven’t met the right woman. Perhaps I don’t really want to settle down. My concern is that, because I’ve been single for such a long time, I often feel like I don’t need a long-term partner at all, and that’s dangerous. Thanks – your advice is greatly appreciated.


Thanks for writing in. First of all – it does not matter at all what other people think about you … so don’t worry about that. Your issue (if you even have an issue) is that you don’t really want to be alone as you grow older … and that is perfectly normal to feel that way.

I’ll be honest with you, I do not think you have a problem. You just have not met “the right woman” yet … and I say that because if you did, then you would want to spend a lot of time with her and settle down together. So my advice is – keep churning until you find the right one.

Now you could always carefully consider what you think you want in terms of a woman – and then make a proactive and deliberate effort to zero in on one like her. Best to identify what you think are your most ideal qualities in a woman … maybe select a “Top 5 Qualities”, and then try to find one that has all or most of those characteristics. For example, for me – the top five would be 1) Latina; 2) High integrity; 3) Gainfully employed in a career; 4) Good-looking; 5) Positive mental attitude. Your “Top 5” characteristics might be drastically different … some people put other attributes into their “requirements” like large boobs, Brazilian waxed, zero children, etc. but that’s up to you. And if you can get four out of your top five in a woman – then that is pretty good. It really is all about identifying the best type of woman you want, and then doing what is necessary to meet that woman.

There is a section of midlifebachelor.com that goes into how to create a recipe for midlife bachelor relationship success that I think you’ll find helpful:

Develop a Strategy for Midlife Bachelor Success

You also might read this section after you first read the above:

Reaching Midlife Bachelor Equilibrium

Hopefully you found this helpful. I encourage you to consider joining our Midlife Forum here on midlifebachelor.com … where we talk about a lot of things, including dating and midlife crisis issues. We’d be happy to have you as a member of our community. Here is a link to it:  Midlife Forum

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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.