No Luck Online Dating?

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 have no luck online dating, and need some advice about dating guys in their 30s and 40s!  Your website seems like the perfect place to garner advice, as I am newly single and have been dating men in this age range.  As I live in a smallish town without many prospects, I’ve turned to online dating.  And what a boost it was to have so many men emailing me!  I had no lack of dates from online, and had tons of fun – but I have to say that my success rate in this age range has been absolutely zero.  When I dated in my 20s, men always seemed to want me, and I took it for granted.

But now, I’m not sure what’s going on.  I’m


an attractive woman (long hair, slim and athletic, and everyone tells me I look like I’m 26, not 36), have no children or any other baggage, and have a good, sweet/fun personality, awesome job, etc.  All of my dates have been fun and never a lag in conversation.  But of my last 7 dinner dates, only 2 have led to second dates.  But after those first and second dates, I never heard from them again!  I would almost understand if I was rude, unattractive, or a bad date – but ALL of those dates went well.  After 6 failed dates, I even went out with a man who was 46 y/o, thinking that, at the very least, he would be happy to date someone 10 years younger!  And well, never heard from him again either.

Needless to say, my self-esteem is in the toilet.  I keep wondering what I’ve done wrong. So my question is, am I too “old” for these guys?  Are most guys in their 30s/40s still looking for women in their 20s?  Because I had great luck dating in my 20s, but suddenly, at age 36, no guy seems to want a second date with me.  If I were still 29, perhaps I would have more “value” in the eyes of these men.

Even in your advice column, you applaud other men for their “younger” girlfriends – is it really so important?  What age range do I need to target?  I feel disheartened that men my age look past me to my younger sisters.  And I don’t want to date a guy in his 50s.  So where does that leave us 30-something women?

Any advice is much appreciated, thank you!


Thanks for writing in – and especially thanks for including the photo.  I have to say … WOW … I think you are an absolute knockout.  I know you said you live in a small town, but if you lived on the West Coast, you’d have no problem finding a large number of men to go out with.

So – based on what you said, it is pretty hard to know what to suggest.  I can make several educated guesses … which I’ll share.  IT COULD BE that you are so good-looking for your small town men that you intimidate these guys.  IT COULD ALSO BE that you are so intelligent (which I can tell from your writing and grammar) that this intimidates the guys.  IT COULD ALSO BE that you need to try to be a bit more WARM during the dates … maybe by touching their hands, or giving them a kiss, etc.  Or IT COULD BE that you are dating beneath yourself … also known as “bottom feeding” … where the guys know they have zero chance with you.  It could also be something you are doing on the date itself – such as talking too much?  Or it could be come combination of any of the aforementioned.  Or it could be something else that I’m not thinking of right now.  It is very hard to guess – without knowing you, personally.

It could also be that you just haven’t cycled through enough guys … especially if you live in a small town, there just not be a ton of men to date.  Consider expanding your dating radius – if you were willing to date someone before who lives up to 20 miles away, then change that to 50 miles … or if you really live out in the country, maybe try 100 miles.  Know also that online dating does require a lot of time, and a lot of “false starts” … so it is not necessarily unusual to have to go out on 20 or more “first dates” before you meet someone you really like.  And sometimes you might THINK you like someone … but after 3 or 4 dates … maybe even after fooling around with them … you then decide NAH (for whatever reason).

Dating is hard work – but I think you are up for the challenge.  You are certainly very attractive and intelligent … so you get extremely high marks in my book.  I’d say just keep trying.

I’m not sure which dating sites you were using, but you since you are very hot and intelligent, in addition to the obvious dating websites (shown on our Online Dating Discounts page), you also might consider giving the following site a try – as it caters to the wealthy, and I think you might do well if you target that particular demographic or type of man:

For some tips on how to most effectively meet someone wealthy there, see our article entitled, How to Meet a Wealthy Man or Woman on  Good luck – please report back with how things go.

What do YOU think – do you have a better answer or a comment?  Use our COMMENT SECTION below, or you can feel free to discuss this in our Midlife Forum.

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.