Dating a Younger Man

"Should I Go For This Much Younger Man?"

July 2, 2012

This question is from a Group Therapy post in our TrèsSugar Community. Add your advice in the comments!

So, for the past year, I have been friends with a much younger guy . . . like 25 years younger. We are together constantly due to work. We travel together and most weeks are together five or more days, 24/7. It has definitely turned into a much deeper relationship than working together. However, neither one of us has made a move for anything else to happen. I don't want to lose the friendship we have or look like a ridiculous older woman. But, on the days we aren't waking up in the same place, it's his texts I wake up to and his texts I fall asleep to. I am totally confused. Is he intimidated by me? Is it the age thing? Should I just let this one go?

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6 Comments

steph1234 45 weeks 6 days

As long as neither of you are married or in a relationship...and he's at least 18....i say go for it....or at least ask him what he thinks of the 2 of you. you'll regret never finding out.

henna red 46 weeks 5 days

I agree, don't screw up your work. I would pull away a bit, make a little distance and see how he reacts. I believe if he wanted more, he would approach you. The road can be a very lonely place, and it's natural to grow close to a friend you share so much time with.But if your closeness has not led to discussions of your personal, intimate lives, and if he hasn't used that as a springboard for jumping into something more intimate....then I'd back up the bus, and leave it alone.

Aquadave 46 weeks 5 days

Don't screw up your working relationship. Also a big difference between older men and younger women and older women and younger men. Women are way more mature than men. That's why older men and younger women get along better, they're closer in maturity where as the other is father apart..

spicegirlnow 46 weeks 6 days

All good comments. No...we don't flirt..it's not how we are. But is he always there..yep. A couple weeks ago I got in an accident on our day off. He showed up and was there all day. He's very quiet. But once we are out and has a couple drinks we talk all night. I have a great social circle. I am a well educated professional so that's never been a problem. It's just something that after all this time that I didn't imagine or see coming.

DazzleDe 46 weeks 6 days

Does he flirt with you? Find ways to compliment you? Does your gut feeling tell you that he likes you as a friend or something more? Whatever the answer is, it's still a working relationship and your employer may have policies regarding intraoffice romances - especially if you are his manager (hopefully not!). If you find out you both want to take the relatinship to the next level, you may want to work out a situation where you aren't traveling together 24/7. I don't really think age is factor for this one.

BiWife 47 weeks 5 h

be careful not to treat this like a teenager. if he's 25 and you're 50, you both likely have VERY different emotional responses to what's going on. While his texts may be the thing that you fall asleep to and wake up to, it could be totally normal, platonic communication for him. It's also easy to feel overly close to someone that you work with day in and day out. The relationship you have might have some undertones of sexual tension, but that doesn't usually translate to an actual, healthy sexual relationship. Don't dip your pen in the company ink, used to be the saying, but since us ladies don't have "pens"... you get the idea... This just sounds like a potentially explosive situation if you try to push it one way or another. Take it too far and he'll shrink away, afraid to talk to you since you misread his previous communications. Find some other social outlets, don't let yourself get into a rut where he's attractive mainly because he's your primary social connection.

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