Skip Nav
Celebrity Kids
Jensen Ackles and Jared Padalecki's Kids Are Already Forming Their Own "Gang"
Celebrity Snapchat
80+ Celebrities You Should Be Following on Snapchat
Kella Ripa
Photo Proof That Kelly Ripa Has Been Smiling Since 1993

Group Therapy: Dating an Older Guy

I just recently got out of a six-month relationship. What was supposed to be a minor break, so that he could manage his time better, turned into a messy breakup that left me totally turned off from the relationship. Thus, I found myself ready to date again much sooner than I would have thought. Almost instantly I was asked out by a guy who goes to my college. He already has his bachelor's degree, but is now getting a degree in nursing. I'm currently working on my masters. But we haven't actually met yet (he found me through our school's network on Facebook, and then on MySpace). We have our first date set for this weekend.

I'm excited about dating again, however, I feel a bit wary about the fact that he's 29 and I'm 24. The five-year age difference isn't so drastic, but all the guys I have dated have always been just a few months older than me, so I don't really know what to expect. I consider myself to be a high-achiever, someone who is serious about her career, but I also have a very silly, girly side. He seems to be very introverted and a high-achiever as well.
Does anyone have any insight on the best way to play my date this weekend?

[EDITOR'S NOTE: To be involved in more GROUP THERAPY, click here]


Around The Web
Join The Conversation
anglebeauty anglebeauty 7 years
Dating a guy who is 29 years older? hi everyone I very need your guys opinion.......please help I met this guy on a dating website his age on his profile is 48....but he look like 40 years old. I'm 29 years old woman who is very young looking..a lot of people would say i'm look like 20. at first.....i thought just being friend should be ok.......we chat on line, talk on the phone......and see each other on the webcam(i live in the east coast, he live in the west coast) I have to admit that the chemistry between us is very strong...he is also very young looking for age 48......everything is going well until we planing to see each other in person. he seem like a very nice person...i very like him a lot if everything he told me is real I won't have any problem being in a relationship with him. But last night he decided to tell me his real age.....I was shocked......he was trying to explain that he never meant to lie or hurt me....he said he is very young at heart and soul but no one would want to even chat to him if they know his real one would give him a chance.....he said my point is I very want to have a beautiful family soon with some one who i can grow old with me to see our children grow. I like to be with on older guy...but 29 years older???? I'm not sure about that...that fact that i very like him make it so hard to decide please give me some thought or advice
haiitsashley haiitsashley 7 years
Just BE YOURSELF and have fun! That's what dating is all about! Age shouldn't matter, especially if you find that the two of you get along really well. Don't think about it too much. Life is way to short. Good Luck!
haiitsashley haiitsashley 7 years
Just BE YOURSELF and have fun! That's what dating is all about! Age shouldn't matter, especially if you find that the two of you get along really well. Don't think about it too much. Life is way to short. Good Luck!
aprilmayjune4 aprilmayjune4 7 years
Age doesn't matter. Social skills do, and some people never quite get the hang of them. I'd be more concerned with the fact that he asked you out through the internet. Did you guys talk on the phone at all before you agreed to meet? It could just be me, though- I've had a lot of bad luck with men I've met from the internet.
LadyAngel89 LadyAngel89 7 years
Age is just a number, can't help the day you were born :) But seriously, if he's going to like you, then he should like you for who you are right now, not who you might be or are going to try to be. Be honest and hope for the best, that's the best anyone can do.
brdwaystarlett brdwaystarlett 7 years
Darling girl!! Don't even worry about it. Honestly. 5 years is piss in the pot. My man and I are 7 years apart (he's 29; I'm 22) and because there's incredible chemistry and a deeply seeded friendship, we've been going strong for over a year. Age was a worry at first. But, truth be told, he finally realized that so long as we're on the same page, that's all that matters. It's your first date. Chill. Breathe. And have a great time! IF it doesn't work out, it's not the end of the world.
GScott86 GScott86 7 years
Ignore the age difference. Be yourself, don't be fake. Have fun and don't worry. Get to know him and what type of person he is, etc. He's not everyone else you may have dated. He's his own individual. =) Enjoy your date.
ilanac13 ilanac13 7 years
well the first thing to realize is that age is just a number, and regardless of how old you are - there's a lot that can vary based on how you live your life. i usually dated guys within 2 years of me, and in college, while i was studying abroad i met this guy who i thought was about my age and it turned out that he was actually 4 years younger than me. that just goes to show that regardless of real age, you can find things in common with just about anyone. now i'm in a relationship with a guy who is 9 years older than me, and it's really good. you realize that you can be in the same place in your life as someone who's older, and i think that it's nice to be with someone who has a different perspective on things. just go and enjoy and don't think about how he's older - just think of his as a guy who has similar interests and all that. GOOD LUCK
Berlin Berlin 7 years
i have 6 years difference between me and my sweetie. He's very introverted and an over achiever too, and I'm a very hard worker, much of an over-achieer myself, career oriented but I do have my fun, girly, silly side too. He may not understand it and he isn't really ever that way, but it's what he loves about me. So be yourself on the date and do what you would find enjoyable and what you would want to do with a partner. If it isn't his thing then at least you know now instead of trying to adapt yourself to being like him upfront. Yes we all compromise but you should certainly be your absolute true self upfront, and then it gives him the opportunity to see what you are like instead of the rendition you give him.
luisamapacha luisamapacha 7 years
You're worrying way too much about this. You haven't even met the guy yet! Remember that people put their best pictures on Facebook . . .be prepared to not even recognize him. I've dated guys 5 - 6 years older and 5 - 6 years younger than I am. The only thing that matters is how mature they are and where they are in their lives.
Lele777 Lele777 7 years
My husband and I are 5 years apart and it's the best relationship ever! Men mature slower than women and we are at the same place. It's great! Go have fun and don't let the age thing put a damper on things!
princess_eab princess_eab 7 years
I think you are WAY overthinking this!! Just be yourself. That age difference is absolutely nothing. Until my current boyfriend, all the guys I dated were 4-5 years older than me. (I'm 29 now and my bf is 2 months younger.)
Deidre Deidre 7 years
Age isn't really the thing -- it's all about being at similar Life Stages. That is, being in the same points in your life where your priorities are similar. At least, that's what makes a lasting relationship. (Anyway, this may just be me, but I'd be more put-off by the fact he tracked me down via Facebook and then MySpace to ask me out; not the age difference. I'm just saying...)
k8-rckstr k8-rckstr 7 years
be yourself... its too hard to try to be someone else besides, if you click you want it to be natural. if you're putting on a show and feel like you're clicking because you're not acting like yourself, the relationship will never last anyway.
Nitachequita Nitachequita 7 years
You haven't met yet and you're worried about a five year age difference? I think you're jumping the gun. Just see if you click first. Five years is nothing, and won't determine whether his personality meshes with yours.
cubadog cubadog 7 years
The headline was a little misleading. I was expecting a 40 year-old not someone that is only a few years older than you. Just have fun and get over the age thing it really isn't a big deal unless he is old enough to be your grandfather!
brookberrys brookberrys 7 years
I was 19 and he was 30 when I when on my first date with my boyfriend (we've been together for 5 years now). The age difference was an obvious issue that we both addressed not far into the date. But after that, it hasn't been an issue at all. I'm mature for my age, he's immature (as most guys are :D) so we feel like we meet in the middle. We have the same goals in life, and we get along great. The age difference just isn't an issue for us.
MandyPinecone MandyPinecone 7 years
i'm married to a great guy who is much older then me. jusy have fun you never know how things will turn out.
cravinsugar cravinsugar 7 years
BE YOURSELF! and have fun. if you aren't yourself, and the relatoinship progresses what will happen when you are too tired to be someone you're not?
skigurl skigurl 7 years
when i was 24 i started dating a guy who was 29 and it made no difference have fun, and i bet you will find he also has a silly side, because most people do (and if he doesn't, is he a guy you see yourself with for a long time?) truly, it doesn't seem like you are in very different places, so don't think about it at all and just do what you'd normally do on a date and be your charming self the only thing i could imagine might be different is that he might be thinking marriage/family sooner than you (if either of you are thinking that at all)...but in my case, the 29 year old was totally in NO rush so it can be good to be with an older guy, as guys are often less mature than girls anyway
karlotta karlotta 7 years
That's nothing! Especially because, as Fallen has pointed out, men at that age are so incredibly immature (for the most part), that you'll probably still find yourself eons away from him - but the other way! (I'm kidding; but actually, you may just find that it's the perfect difference for you guys to be on the same page!) Don't sweat it, five years is nothing. He'll be a bit more worldly, mature, in touch with himself, and interesting than the regular guys!
Nina_79 Nina_79 7 years
ps: not having seen him in person yet I would not say to much about how he is. I think you might just be a bit nervous to meet him and maybe not as ready to date as you thought you were. But really here the age difference is not very big and age is just a number and it's the person that counts.
Nina_79 Nina_79 7 years
In the big picture 5 years is nothing.
The-Drunk-Lady The-Drunk-Lady 7 years
I don't think dating someone older is anything to be worried about. I've dated men, whose ages were up to 15+ yrs older. I found it wasn't about age, it was their personality that mattered. Look at your date as going out with a new friend. It takes the focus off of "is he going to like me?; I hope I don't do something or sound stupid" and all the other first date jitters. Don't sleep with him right off. I'm sure you already know that, but wanted to add it anyway. Don't stress about your silly side. It's who you are, so don't hide it. I'm sure you'll know when it's appropriate to show it. If he doesn't appreciate it, then that's his problem. Never change who you are because you think the other person won't like you. Stay true to you. Both of your majors are in the medical field, so you have that to talk about. I'm sure you'll have other things in common also. So, relax and have a great time.
hope2be hope2be 7 years
The whole point of dating is to get to know someone and HAVE FUN. So don't take it too seriously and don't even try to emphasize on age difference. My fiancee is much older than me (more than a decade older), and I took a chance dating him without even wondering about age difference, I was just dating around (I was dating another 2 guys beside my fiancee at the same time, but only lasted with my fiancee). It's just how you 'mesh' with each other anyway, sure there'll be some difference in taste of music or whatever, but if you guys are in the same place, want the same thing, can enjoy each other aside your differences, you're in a good place. Have fun this weekend!

POPSUGAR, the #1 independent media and technology company for women. Where more than 75 million women go for original, inspirational content that feeds their passions and interests.

From Our Partners
Latest Celebrity & Entertainment