Why my flirt won't ask me out

iVillage Member
Registered: 12-19-2001
Why my flirt won't ask me out
3
Tue, 04-30-2013 - 5:30pm

I usually have lunch on nice days out in my vehicle to get away and enjoy the sun.  Today I had a total shocker when "MB" showed up and sat in my vehicle with me while we ate. That is the first time he's ever done that. We were talking as we always do and the topic of his last girlfriend came up.  I told him that I thought it was strange that after 14 months of dating he never had his mother meet her.  He told me that one reason was because he always felt something wasn't quite right about the gf (Turned out she was a little loony and even tried to trap him into marriage with a fake pregnancy).  And he said that he is very protective of his mom..... she was all he had as a child because his father wasn't around. He said he knew his mother wouldn't like her and that his mom always told him not to get involved with anyone that was married before or who had children.  GF struck out on both counts.  I think in a roundabout way he was telling me why he won't ask me out.  I strike out on both of those PLUS I'm 13 years older then him and only 10 years younger then his mom. I do sort of get it.  On the other hand I hope that all I will ever want for my only son is for him to be happy.  He said he's recently told his mom that at his age now (39) it will be hard to find someone that hasn't been married.  I didn't really know what to say to that so I told him that my parents did not like my ex but they just wanted me to be happy.  And that is the truth, they never liked or trusted him.  No way I want to get in a competition with mom.  That usually does not end up with good results. But it does lessen the confusion on my part.  I couldn't figure out why he kept flirting and saying all those things to me and yet not ask me out.  He's probably been more confused then I!

iVillage Member
Registered: 02-25-2013
Wed, 05-01-2013 - 9:59am

You should avoid him for several reasons. First of all, he's a Mama's boy. What Mama says will always trump what his gf/wife's wishes are. A 39 year old who has to get Mama's approval of who he dates? Ridiculous. Another reason: He has the confidence to ask someone out, since he's done so in the past. He is not shy. He flirts. Therefore, he would ask you out if he wanted to date you. He does not. He likes the ego boost of a woman who has a crush on him. It makes the day more fun. He's a cat and bats you, the toy, around all day, and you stick around for more.

If this is your co-worker, starting treating him like just any other co-worker and discontinue the emotional affair. If he continues flirting, tell him the truth. If he's not going to ask you out, it's frustrating to you and it needs to stop. You're on a merry-go-round that's getting you nowhere. The time and energy you spend thinking of this man could be spent on someone who is actually worthy of you and will ask you out. If you're having trouble meeting men, go tto meetups.com and see what activities are going on in your area. Good luck.

iVillage Member
Registered: 11-28-1999
Wed, 05-01-2013 - 7:15pm

I had just about the same reaction.  I thought you were going to say that he was 25 and then when I read 39, I thought--are you kidding?  Does he live in mom's basement?  Certainly a man that age shouldn't be doing anything hurtful to his parents but it's not their decision who he dates or marries.  He doesn't need to protect his mom. If I do the math right, she's 62--that's hardly decrepit.  I'm 55 & my mom is 87--maybe i need to protect her from some things, but a 62 yr old woman should be living her own life.  And seriously, at 39 and counting it's going to be harder for him to find a woman who has never been married or had kids unless he goes back to dating women in their 20's--and most of them don't want an "old guy" for a boyfriend.  I don't think you should waste any more time thinking about him--he sounds like he's emotionally not grown up.

iVillage Member
Registered: 12-19-2001
Sat, 05-04-2013 - 9:27am

I certainly realize that things are not going to advance any further for us.   I have a lot of issues stemming from past relationships (trust, low self eteem, too independent, etc.) and I will definitely need a manly man.  As sweet as he is and even though we have tons in common I don't think he could "handle" me even if he ever grew the balls to ask me out,.  I was fine on my own before he had to open up his big mouth and confess he had feelings beyond friendship for me and I'll be fine again. Right now I'm just in a state of depression over everything.....past, present & future.....but this soon shall pass as well.  I just need to redirect myself back to where I was prior to him and stay on my goal of getting my home in order so when the market goes back up I can pocket a nice profit.  It's kind of  hard since I have to see him every day but in a few months my office will be moving so hopefully I won't have to see him except for when I hand out paychecks.