Dating again. 40+ after 20+ years marriage.... I think I have a 'suitor'?

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iVillage Member
Registered: 01-18-2006
Dating again. 40+ after 20+ years marriage.... I think I have a 'suitor'?
Tue, 10-01-2013 - 6:54pm

It has been a loooooong loooooong time & I never dated much as a teen/20+.   

I think I might have someone who's interested in me.   Maybe Im totally naive.   I dont know WHY I cant BELIEVE that anyone would be interested in me, but that's it.   Thus, Im finally motivated to write this on the bulletin board.

Im late 40s.   Guy's late 30s.   Neither of us are bad looking & we seem to get along well as friends.  We seem to communicate well.    And I do enjoy being around him.   I suppose he does me.

Here's the deal:  He's been my "maid", yes, housekeeper for about 1 1/2 years.   He has watched me go thru a the depths of hell when I found out my husband was cheating, has watched me finish school & look for a job.   

Anyway, I never thought tooooo much of him - except sometimes lately.   I waver.   And, of course, it's been a looooong time since Ive had sex.   Sometimes I find myself thinking about him.   Sometimes not.

So for the past few months, besides cleaning, he has helped me pack stuff in getting ready to move.   And he's helped me very much lately, as he knows we now have a moveout date.  He seems really in to this moving project.   I pay him, of course, but in my opinion, he doesnt ask for what a professional would whatsoever.

So he's been spending lots of hours - helping with the move, cleaning, packing etc.   with or without me.

He is very respectful & has helped me manage the timing & procedures, etc.

Today I sent him over to clean up after the painters.   He cleaned the place top to bottom.   For $ of course, but later we talked on the phone & he told me about what a good job he did & that he thought Id be good with it.

My vacuum broke & he today actually brought one with him.   We ended up not using it - but I did ask him - who's vacuum was it.   He said it was his.    

Silly thing - a vacuum cleaner - but the fact that he'd bring his own to do my stuff???    that seemed a little "off" to me.

Every once in a while, we'll text - but it's pretty professional & totally friend-like.

I dunno.   He just really wants to help me with this, as he knows Im struggling, mostly due to the divorce.   I cant understand why he'd wanna get tangled up w/me and any of it.

Do you think he likes me?   I like him - but it's not strong or anything & there are others I like, but he seems to be the one around (right now).

What do you think?   Am I being totally naive?

iVillage Member
Registered: 01-02-2008

I had to chuckle at NAD215 comment..

I say go for it and ask him what his intentions are .. If he wants some booty then that is up to you if you can just accept that. Heck you can always replace the help.. It does remind me of the new series Devious Maids.. LOL

Anyway;; the ball is in your court.. do you want a relationship and if you do then ask him outright.. If he wants bootie ask him? If that is okay with you then you have to decide.. If not then he stays your help...and you move on to other opportunities..


iVillage Member
Registered: 09-29-2003

Oooohh! The maid! How deliciously scandalous!

Sorry, I couldn't help myself there. I'm seriously not poking fun. It just sounds like steamy excitement to me. :)

What is this gentleman's situation? Is he single? What personal information do you know about him? I would say until you find out more to proceed with caution. At the end of the day, you are his employer. How would you feel about losing him as an employee? Is he replaceable?

It sounds like he is pretty professional with you and doing his best to help you through a tough time. I think he sound like a nice guy but at this point it is difficult to tell if he wants more. Has he given you any sign of interest? (And no, I don't think bringing over his own vacuum cleaner counts- sorry).


iVillage Member
Registered: 11-28-1999

Remember that old TV show with Tony Danza, Who's the Boss?  Tony was the housekeeper & they ended up together.  I think that probably only happens on TV.  I'm not saying that it couldn't happen.  I'm sure he likes you but as what?  You're his employer--from that, he probably has developed some feelings of affection toward you if you have spent some time together, maybe he's even attracted to you--but from what you said, he's basically just working.  has he ever said anything to you that would make you think that he wants any kind of relationship other than work?  Has he said flirty things?  Has he asked to spend time with you outside of work?  I'm not trying to be mean, I'm just asking you to look objectively and hopefully you won't be embarrassed if you come on to him.  

I do have to say (just so you won't feel too bad) that when I first got divorced from 1st DH, 17 yrs ago, I developed a crush on my boss who was single & my age.  We even used to hang out sometimes--go out to eat or to the movies.  Somehow in the back of my mind, I really knew that the crush was some kind of diversion from the divorce.  I even told my boss years later about the crush and he said that he never knew.  I'm glad nothing happened because of it because I'm still working for him--it probably would have been bad if we ever dated.