Is a 28/29 year old man too old to date a 21 year old woman?

[Acvskdtm]

I don't think that is necessarily too much. If you get to know her better you may discover a maturity difference or that you're at a different place in life, but 21-28 is not always that different. It could very work out depending on the two people and their situations. I would give her a chance.

[Krankor]

If you were 38 and she was 31 it wouldn't even be something to bat an eye at. As it stands, 28 and 21 still isn't a big deal--there is the potential for a maturity gap, but that's why you go on dates first and get to know each other rather than dive headfirst into a relationship.

 

The co-workers thing is a bigger potential issue. And you ARE coworkers, even if you don't work that closely together or see a lot of each other. Chances are, a 21 year old cocktail waitress isn't going to be there forever, but you never know for sure. So in your circumstance, I'm not definitively saying don't do it, just be prepared for some awkwardness and even being made fun of behind your back if she rejects you. Or, if you do date and things don't work out, having to see her even in passing won't be easy.

 

It sounds like you've already made up your mind that you want to pursue this, so good luck. You should maybe try talking to her and flirting a little first though--test the waters a bit. And don't get too hung up on this one girl. Get on a dating app if you aren't already and talk to a few--make her just one of several prospects.

[Goten]

If you were 38 and she was 31 it wouldn't even be something to bat an eye at. As it stands, 28 and 21 still isn't a big deal--there is the potential for a maturity gap, but that's why you go on dates first and get to know each other rather than dive headfirst into a relationship.

 

The co-workers thing is a bigger potential issue. And you ARE coworkers, even if you don't work that closely together or see a lot of each other. Chances are, a 21 year old cocktail waitress isn't going to be there forever, but you never know for sure. So in your circumstance, I'm not definitively saying don't do it, just be prepared for some awkwardness and even being made fun of behind your back if she rejects you. Or, if you do date and things don't work out, having to see her even in passing won't be easy.

 

It sounds like you've already made up your mind that you want to pursue this, so good luck. You should maybe try talking to her and flirting a little first though--test the waters a bit. And don't get too hung up on this one girl. Get on a dating app if you aren't already and talk to a few--make her just one of several prospects.

 

I haven't gotten around to talking to her yet, as I took some time off of work for personal reasons. There are several women at my job that I like, lol. But it seems as though many here are warning me against pursuing any girls at my job. As for online dating, I've never been a fan, though I admittedly haven't tried it. I heard it's hard for guy's to get decent looking girls with no kids when it comes to online dating. I suspect the most attractive ones with no kids are very picky probably because they have hundreds of guys messaging them.

 

Regardless, I'm still thinking of at least trying to get to know this girl first, despite a few people here warning me not to. If she's not interested, then that's that. But maybe she will be. Even though I'm 28 turning 29 in July I look about 22-24 (I have no facial hair). I wouldn't lie about my age, but I've been told I don't look like I'm pushing 30, so hopefully that's a good thing.