Is he hitting on me? (long post, sorry!)

iVillage Member
Registered: 10-11-2012
Is he hitting on me? (long post, sorry!)
Wed, 12-12-2012 - 11:48pm

I feel so dumb. I am recently separated and have not dated in 10 years. I used to be pretty good at this! I think a slightly older man (he's 51, I'm 33) from work has been flirting with me, but don't want to look like an idiot if he has just been being nice. We are not exactly equals in the workplace, but he is not in charge of evaluating me or anything.

For the past 3 years, he has asked me a lot of personal questions about myself. We've had somewhat of a "big brother-little sister" relationship going for the past couple of years. He jokes around with me a lot and plays pranks on me. A year ago he asked me to give him my cell phone so he could put his phone number in it. He has not given his number to any of my other coworkers. He always makes a point of having a brief conversation with me whenever he sees me at work, no matter how busy he is. He compliments me often. We text outside of work. We've gone to coffee a couple of times.  Recently we were at a social function and he kept texting me to come find him so I could meet his kids and siblings. He mentioned multiple times the next day that he was so disappointed I didn't get a chance to meet them.  

That all seems pretty obvious that he likes me, right? Here's where it gets confusing. I kind of think I might be stuck in the "friend zone." He asks me to watch football with him (I'm a big college football fan) and he does things like belch in front of me, punches me in the arm, you know...things he might do with a guy friend. We've been alone together and he has never tried to make a move on me, even when we were sitting very close. Granted, this has generally occurred at work.

I'm having fun having a little bit of a crush on this guy, but can't tell if he's interested in taking things a bit further. How can I go about finding out now that I've been his "best work buddy" for the past couple of years?  If he doesn't actually like me, things at work could get really awkward.  No one at my work knows I am now separated, except him. He does not know any of the details. Maybe I should just enjoy this for what it is, a crush on a guy who is safe because he doesn't reciprocate.  I think a small part of me is just hoping he's attracted to me too because it's been so long since I've felt desired. 

Community Leader
Registered: 07-16-2001
Thu, 12-13-2012 - 11:47pm
I think if he were hitting on you, you wouldn't be asking us about it. Whether he's interested or not really depends on his beliefs. Separated for two months, regardless of when the marriage was "over", isn't long at all. If he is interested, it's wise for him to hang back for awhile. In addition, the age difference might make it more of a fun thought for him and not something he's willing to follow through on.
iVillage Member
Registered: 11-28-1999
Thu, 12-13-2012 - 4:45pm

I'm not sure that it ever gets easier.  When I got divorced around age 40, I thought men would be more mature & it would be easier.  HA!  I do think that if you like someone and you don't feel comfortable directly asking him out (which I don't) you do have to give him a bit of encouragement.  Since you are leaving maybe you could wait til it's closer to the time you leave the company.  Good luck.

iVillage Member
Registered: 06-03-2009
Thu, 12-13-2012 - 12:55pm
It could be that he is interested, but hasn't made a move because you haven't been separated long and he doesn't know if you're even open to dating. Have you given him any indication that you are ready to get back out there? Maybe in casual conversation mention something about a friend offering to set you up and how you're rusty, but it sounds fun. That may be all the encouragement he needs to be more direct with you. He also may not be sure you're open to dating a guy his age. 18 years is a wide gap and contrary to what the media portrays not every pretty young thing is jonesing for a much older guy.
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iVillage Member
Registered: 10-11-2012
Thu, 12-13-2012 - 12:46pm

Thanks for your responses. I have only in the past 2 months become legally separated. The relationship has been over for 2 years, but out of respect to my ex-husband and my family, as well as for my own healing purposes, I have not had any interest in dating, flirting, etc until now. The divorce process in my state requires a minimum of 6 months separation prior to divorce. I'm not looking to start a new relationship right now, but would definitely be open to some companionship and see where it goes. 

In answer to your questions, we will only be coworkers for the next 6 months. Then I will be moving on to a different phase in my career. At that point it wouldn't be as awkward for me to just ask if he likes me or not. Until then, probably a little uncomfortable if the answer is no. We have several mutual friends, most of whom are couples that we hang out with outside of work, so no, we're not generally alone. I'm not certain he is straight. I've never asked, but would assume he is since he has dated several women in the time I have known him. He was married for 25 years. 

I guess I'll just have to see if he makes a move in the next few months. If he doesn't, I'll assume he doesn't see me as more than just a buddy. I've never really had to be the one to make a move first, so I'm not sure I will work up the courage to do that. I would just hate that to be the reason we didn't explore things further. I feel like a junior high girl, which is why I have not uttered a word of this to any of my friends in real life and have turned to the anonymity of the internet for advice.  Not sure if I'm ready for that kind of ego bruising.  Hopefully this gets easier with time. Dating is just like riding a bike, right???

iVillage Member
Registered: 11-28-1999
Thu, 12-13-2012 - 10:42am

I assume that you aren't watching football games at work--you must be alone together then, right?  I would think if he was interested, after he found out that you were separated, he would have shown some kind of romantic interest.  however, there are people who don't want to date someone who is separated & not divorced because they don't know what's going to happen--will you get back together w/ DH or not?  What is his story about relationships?  Does/has he ever mentioned dating anyone?  Maybe he's also been divorced and just not that interested in a relationship.  Maybe he thinks you are too young (most guys in their 50's would be dying to date a younger woman, but there are exceptions and 18 yrs is not "slightly older.")  What I think is that if he is interested, he would ask you out.

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iVillage Member
Registered: 05-14-1999
Thu, 12-13-2012 - 9:46am

My apologies if this is duplicated.  This is my third attempt.

How long have you been separated?  If you've been hanging out for two years and have been separated for a while it would be odd if he hasn't acted on any potential feelings he may have for you.  I don't necessarily think that he has romantic interest based solely on the fact that he wanted you to meet his family.  Are you sure he's straight?

How do you feel about becoming involved with a co-worker? 

This may be one of these situations where, you'll either have to wait for him to make the first move, or make one yourself.