This dilemma pops up in my mind a lot. Not for me, for my brother.

Call me a doting (annoying) older sister. Call me whatever you want, but I am wondering if maybe my readers can help me understand the dating world after age 25, or rather mid to late twenties.

You see, my brother is 25 years old. He’s currently studying to get his masters in Education. He’s smart, very good looking (ok, I might be biased, but he IS), in great shape, and the kindest soul I know. The issue?

He’s single. Like has been single for a long time.

He used to work with all married elementary school teachers. Not much opportunity there. Now he’s in school full time, but his program is small. I get the feeling there’s like one eligible lady, and every guy in the class wants her. He’s not the type to play the field. In fact, he is a pretty shy guy. He says that he’s looking for a nice girl with similar interests and priorities. I used to think he wasn’t looking in the right places, or he was being way too picky. But now I am wondering if it’s a mixture of being picky and a lack of opportunity to meet new people?

One of his dates that I met (at our wedding) was a “model” (that’s a loose term, apparently) who, I’m sorry to say, had perhaps two or three more brain cells than a potato. She didn’t appear to be a “nice girl with similar interests and priorities.” She seemed like a pain in the ass that would probably cause a lot more trouble than she was worth. I wasn’t too surprised when that went nowhere.

I want him to find a good woman. I don’t want him to miss the window of opportunity at love. He’s young, but not that young. It is not so outlandish to think that if he found “the one” he’d be ready to settle down and soon. I think this quote from When Harry Met Sally (one of my favorite movies ever) kinda sums up some my point:

All I’m saying is that somewhere out there is the man you are supposed to marry. And if you don’t get him first, somebody else will, and you’ll have to spend the rest of your life knowing that somebody else is married to your husband

Is it possible to let love pass you by? Do you have an increasingly difficult time meeting new potential mates the older you get? Is it about putting yourself out there and going after what you want? Or should you wait and be patient? I personally don’t think you should wait for anything to come to you. There is such a thing as being overly-eager, but I don’t think my brother is suffering from that.

What is the deal with dating in your mid to late twenties? I was with L by the age of 21, so I don’t really have much experience with dating after college. I’m curious how you meet people when you are sick of going to bars and clubs, and meeting drunken idiots like my husband. Totally kidding, honey! (I realize not everyone at a bar is a drunken idiot, but let’s face it, most of them are old married farts or they aren’t looking for anything serious.) I’m tempted to start an online profile for him on or some other dating site. Too much?



  1. Reply


    April 27, 2010

    No way, it's not too much! I had the same problem. After college, my social circle wasn't as large, and I realized a year or two out that I had been single ever since my college boyfriend, and I wasn't meeting anyone new. And the people I was meeting (and dating) were MAJOR losers. So I signed up for match and met my husband. ๐Ÿ™‚

    I say he should go for it. Be proactive!

  2. Reply


    April 27, 2010

    Meeting partners online is rapidly losing any stigma it once had, mostly because it's so successful! Going through a reputable site opens up a world of eligible people who, like your brother, just don't have the wide social circle or desire to hit the bar scene. I say do it, or urge him to – it's a great idea!

  3. Reply

    Chic 'n Cheap Living

    April 27, 2010

    Do it! I have a few friends who found serious relationships or marriage through sites like eHarmony, or the like. It's just hard to keep on meeting people esp. when you have such specific social circles and are busy like your brother.

    Ooh and the wedding I'm attending in San Diego in Sept? My cousin and his fiancee met through! You never know!

  4. Reply


    April 27, 2010

    I'd let him set up his online profile, but offer to proof it for him if he brings it up first.

    Is he religious at all? I met my Mister at the young adult (20s, 30s, and 40-somethings with no kids) group at my synagogue, it was so awesome to know that we came from similar backgrounds and have similar religious beliefs because we both chose to belong to the same community.

  5. Reply


    April 27, 2010

    First, online dating is not too much…I know several couples that met online and got married ๐Ÿ™‚

    Second, it's SOOOO difficult to meet someone worth dating when you are in your mid/late twenties. I found myself newly single after graduating law school and without my usual circle of friends (the ex and I had the same circle of friends and I chose to leave so I could move on). I never met anyone worth dating at a bar, but where I did meet several quality guys were at parties thrown by friends or friends of friends. In fact, I met my husband at a birthday party of someone I knew from college.

    So I guess my thoughts are (1) online dating is definitely worth a shot and (2) reconnect with old friends and make an effort to accept every invitation to a party or group event…I think there's a greater chance of meeting a quality person through people you know.

  6. Reply


    April 27, 2010

    Definitely go the online route! I have no experience with it, but would have been open to it if I hadn't met my hubby at work.

  7. Reply


    April 27, 2010

    I totally agree that it's hard to meet someone after a certain age, particularly if your job is of no help since that's where we spend so much of our time. I met my fiance at the gym. Totally wasn't looking for someone, and it just happened. Afterwards however I noticed there were tons of single people there. If that is not his thing, it wouldn't hurt to get involved in things outside of work (church group, volunteer or charity work, a sports team of some kind, etc.). Just some ideas!

  8. Reply

    HisBirdie (Ali)

    April 27, 2010

    I turned to because I worked with older men (and my Dad) and I went to school with mostly women and gay men. It's really difficult to meet quality people at a bar :-/
    I think we should set your brother up with my (also 25) sister ๐Ÿ™‚ She works a lot and doesn't really have time to meet anyone… and she is really shy so she would NEVER put herself on

  9. Reply

    Cheap Wife

    April 27, 2010

    Ugh! Dating stinks!
    I have LOTS of expereince dating at your brothers age. I did not meet my husband until I was 27 (and a half!). I got out of a long relationship at 24. What I did was the best thing for me…it may not work for everyone but it worked for me:
    I didn't really date anyone for 3 years, What I mean is I DATED lots of people but never for more than 2 weeks. After too many years of being with people who were right for me "except for that one issue" or people who had potential but where not "who" I wanted in a mate at that time. I was too old smart to think people will change. I made the decision; "If you are not the person I could marry, as you are right now….then I am not wasting my time." I also felt that being in a realtionship that wasn't right would prevent me from being available when the right one DID come along. So I had 3 LONG years of being single and not meeting the right person and then if happened! I DID put myself out there. You have to. I did internet dating and stuff. My husband awnsered my ad on craigslist of all places. When I met him for our 1st date I knew that he was who I had been waiting 3 years for. After our 2nd date I called my best friends and told them he was the one I would marry ๐Ÿ™‚
    Tell your brother to get out there…..and to be a little picky. Don't waste time dating people for "just now". Date a lot of women but don't commit until it's the right one…hopefully "the one"

  10. Reply


    April 27, 2010

    I never did the dating sites, but I did find myself single in a new City at age 26. I made a promise to myself to accept every offer to go out. It was a commitment. BUT I met the Mister at a bar on a Sunday morning watching football. If I hadn't put myself out there, I would never of me him.

    Good luck. Your Bro sounds like a great guy!

  11. Reply


    April 27, 2010

    I met a lot of people online and dated a couple. Although, not through dating sites. I actually met them through sites like Live Journal and Xanga. I kind of met my husband through Xanga, although we knew each other before, we started talking through commenting on each others' Xanga sites.

    Other than that, I think the best way to meet people is through friends.

    Does he have any hobbies? He could join a Meet-Up group. I've met so many new people since I picked up photography.

  12. Reply

    M and C

    April 29, 2010

    This seems to be a huge problem. I know lots of great single guys over 21 but no single girls. Where are all the girls? That being said, I sometimes think I wouldn't make it as a single person again. It's been almost 7 years since I was single and I don't miss it at all!

    I hope your brother finds a nice girl:)

  13. Reply


    April 29, 2010

    Thank you everyone for your comments, suggestions, and support! This really means a lot because I want to help my brother. Even though dating might seem like common sense, it seems like it gets increasingly more difficult as you age, no?
    @Anne: I have read so many amazing stories about How awesome that you and hubby found each other there. I'm passing the link onto my bro, for sure.
    @koritsimou: Thank you for the words of encouragement! ๐Ÿ™‚
    @Chic 'n Cheap Living: I had never heard of I went and checked it out, and it looks interesting. Passing the link onto my bro! Thank you!
    @violarulz: Yes, I think you're right in suggesting I let him set up his own profile ๐Ÿ™‚ We used to be active church members, but after college, that has somewhat faded. I have a few friends who met through our church group – such a great way to meet people that share your interests!
    @Sandy: Such a good suggestion about reconnecting with old friends and accepting social invites! I actually met L through old friends. I would've never met him if I didn't accept an invitation to attend an art show. You just never know. Gotta keep an open mind!
    @Heidi: Thanks for the support!
    @Adrienne: Interesting! I should tell my bro to renew his gym membership ๐Ÿ™‚ He enjoys staying in shape, and why not meet other like-minded, healthy people? Thanks for the suggestions.
    @Ali: Another success story! Yay! And yes, it sounds like your sis and my bro should meet! Can we be sneaky older sisters and make this happen without totally embarrassing them? ๐Ÿ™‚
    @Cheap Wife: I really admire your ability to put yourself out there, and not settle for less than what you deserve. Seriously, I got a little teary-eyed reading your words. And that's what I want for my brother. I want him to date around a little – figure out what he really wants! Thank you for sharing your story.
    @Sugar: I remember your story (maybe from weddingbee). That's super cool of you to move to a new city, and put yourself out there. It's not easy, but now you have Mr. Peep ๐Ÿ™‚
    @Kelly: I remember when everyone had a Live Journey or Xanga page! I agree about meeting people through friends. His biggest hobby is basketball, but he plays a pick-up league with a bunch of guys! He needs to join a co-ed league ๐Ÿ™‚ Good suggestions, thanks!
    @M and C: I know! Where the single ladies at?! And I don't miss being single either. It's tough out there! Thanks for the encouragement.

  14. Reply


    April 29, 2010

    Hey, I know I'm late to this party, but just wanted to chime in with my experience. I too found myself single in my mid-twenties. At that point I dated a lot, but was finding it hard to find the right person with few opportunities to meet new people (dating in graduate school was hard!) At 26 I moved to a new city for a fellowship and after six months gave the online dating thing a try. Very soon after I met my husband. We dated for a couple of years before getting engaged, but I knew very very quickly that he was the one. I was at the point in my life (and your brother probably feels this way too) where I knew what I wanted, what I could give, and wasn't going to settle for a ho hum match. I sometimes stop and think how amazing and lucky it is that I found my husband… without the internet we never would have crossed paths, and I can't imagine what life would be like without him. So I hope your brother gives the online dating thing a try. I think I was in a very similar situation and know how frustrating it can be!

  15. Reply


    May 5, 2010

    Get him online! I met my ex on To me, it's less 'must get married now' than eharmony or match. Which is nice because there is less pressure, great for mid-20s, I think. Plus it's free! It didn't work out (this time) for me, but he was wonderful and there are so many different types of people on there. Somebody for everybody.

  16. Reply


    May 23, 2010

    I recently came across your blog and have been reading along. I thought I would leave my first comment. I dont know what to say except that I have enjoyed reading. Nice blog. I will keep visiting this blog very often.


  17. Reply


    September 25, 2012

    Your brother sounds like someone i would be interested in! LOL – (I mean that as encouragement that there are still single, mature, women out there – not hitting on him!) Since you posted this 2 years ago, i assume he must have found someone by now! Out of curiosity, what worked for him? I need some pointers! LOL

  18. Reply

    Priscila Baddouh

    November 3, 2012

    I think I want to meet your brother…