Pillow Talk with Diana: “Why Can’t I Find a Girlfriend?”

February 24, 2009     Posted in Advice, Relationships, Sex

Got a question for Pillow Talk? Email pillow.talk.cc@gmail.com and we’ll tackle it next time!


By Diana

Q: Okay, so I’m a guy, and I’m having trouble finding a girlfriend. I’m 20, about 6 foot, 165 lbs, average build, white (but not pale) skin, well groomed, short hair, shower daily. I’ve dated ten women, two serious relationships.  My most serious relationship was two years. I’m not really into sports, but if I’m hanging out with some friends and they’re watching a game, I’ll watch too.  I strongly believe in treating women with respect.

Generally on the first date I bring flowers, walk up to her door to pick her up, take her to her favorite food restaurant, always open the door (even car door) for her, and always pay (I don’t know why girls let guys get away with not paying). I’m more of the romantic nice guy than the hardcore-work-out-football-beer-blah type guy. I’m not into drugs, don’t smoke, and only have a drink occasionally. I hardly ever curse unless I’m mad. I use correct English but don’t correct others for not using it. I don’t have an accent or a lisp.

I’ve been told I’m attractive, hot, cute, average, normal, etc. I think I have a easy going personality, definitely not pushy. I smile a lot and always make eye contact. I love making people laugh, but most of all, helping them.  I have a few close friends, and enjoy small groups rather than large groups. I love to cuddle. I pleasure her before myself, or try, if you know what I mean. I don’t obsess over a relationship and call her all the time, and I don’t get jealous unless the relationship is threatened. I have a clean rep.

I’ve been on a few dates within the last few months, but none of them seemed to develop into anything more than just friends.  That spark never came.  I’ve talked to some girls that I know and asked them to dinner but they don’t seem interested in “that way.”

I’ve tried to think of everything that describes me.  I know it’s hard to figure this out without knowing me, but I do appreciate you trying.  Maybe I’m trying too hard?  Maybe I need to buy a motorcycle and become a bad-ass?  I dunno.  Can you give me any tips to improve my search for love?

A: Dude, chill out. First off, for the record–a few dates over a few months with no spark and a few rejections from girl friends is completely, 100% normal. It’s the natural process of dating and figuring out who you click with and meeting many people with whom you don’t. So just an FYI, your experience is not indicative of there being anything wrong with you–in fact, if you were sparking with every single woman you dated, that would probably concern me more. This is what dating is.

That said, other than potentially being a bit neurotic, there’s nothing really wrong with you, as far as I can tell (and I’ll chalk my “neurotic” assessment up to you wanting to cover all your bases in your letter!). You’ve dated and have held down a long-term relationship, so all signs point to you dating and having a relationship again the the future. Hold off on purchasing a Harley for now, and take a deep breath.

Yes, it’s possible that you’re trying too hard, but I think your real problem is what exactly you’re trying so hard to achieve. You’ve listed all of these lovely qualities about yourself, but what are you looking for in a girl? So far, all I have from you is that you’re having trouble “finding a girlfriend,” and that you’re on the search for love and a serious relationship.

But with who? It doesn’t seem to me that you like anyone in particular right now, and that’s fine–it’s certainly OK to just date around to figure it out what it is that you’re looking for in a relationship and girlfriend. But you seem overly concerned with how you’re coming off and what you bring to the table, rather than what qualities you’re looking for–so in that sense, yes, you’re probably trying a little too hard to please and to be liked.

To up your chances of a romantic connection, why not starting looking for women in places where you might have a higher success rate? I’m assuming you have hobbies of some sort–try joining a group (meetup.com is a good place to start) and enjoy that hobby with a group of strangers. If you don’t have hobbies or interests, get some. If all you’re bringing to the table is being a nice guy you won’t get very far.

Have hobbies already? Try a new one–take a class, join a co-ed sports team, start volunteering for a cause you care about. Instead of going out with the same group of friends, extend your next party invite/bar crawl to your friends’ friends and meet new people that way. Try online dating. Ask friends to set you up in a casual group hangout/date setting. Say yes to invites you normally turn down. And don’t try all of these in one night! Sometimes you just need to shake things up a tiny bit to see big changes.

And in the meantime, stop worrying about finding “a” girlfriend. Enjoy meeting new people, going out, and just dating without all the pressure you’ve been putting on yourself. Have fun!

And girls, this advice works for you, too!

[Image via kcantinmft.com]

22 Comments on "Pillow Talk with Diana: “Why Can’t I Find a Girlfriend?”"

  1. Lauren, University o says:
    Tue, 24th Feb 20098:48 am 

    I agree. Maybe he's not getting girls cuz he only talks about himself and how great he is.

  2. A says:
    Tue, 24th Feb 20099:41 am 

    Hmm bringing flowers & everything is ideally nice, but can sometimes come off as overwhelmingly romantic. I'm not that cheesy of a person so sometimes I feel awkward if a guy is just doing too much romantic stuff. If my bf of 3 years brings my flowers, It's fine because I'm comfortable with him. But I might be embarrassed & not know how to react if a guy I just started dating did.

  3. Mystery says:
    Tue, 24th Feb 200911:28 am 

    Ok couple of points to address so let's get started.

    First off, Sarah. Giving your # away in the comments section of a blog post. Could you get anymore desperate?

    Secondly, to the pussy who write in to pillow talk, you are a pussy. Flowers on the first date, really? Really? How much more of a pushover could you possibly be? Everyone always says "be yourself", which is good advice, but the key is to be unapologetic about it. It was already said, but nice guys finish last. You should be more concerned with having a good time when you're on a date than if you're doing romantic and sweet things. And if all else fails, just ask, "Can I get a female opinion?"

  4. OMGLikeWOW says:
    Tue, 24th Feb 200911:56 am 

    OMG Mystery your comment was sooooo hilarious…

  5. K says:
    Tue, 24th Feb 200912:51 pm 

    Don't become an ass. Just let loose a little.. I'd bet a lot of girls are interested but are put off by the fact that you don't seem to have any flaws. That is scary! We don't want to date perfection, because then we feel like we should be perfect. True story. I agree with exploring more hobbies, you'll find something you're passionate about and hopefully someone at the same time!

  6. Sam says:
    Tue, 24th Feb 20091:14 pm 

    He seems a little too into himself – like he’s putting himself up on a pedestal of perfection. Just my two cents.

  7. Jacks says:
    Tue, 24th Feb 20091:05 pm 

    "White skin with a natural tan?" Does that even make sense?

  8. Ryan says:
    Tue, 24th Feb 20091:48 pm 

    +1 to nice guys finish last.

    Don't do anything you wouldn't do for a female friend, don't show too much interest, never emotionally disadvantage yourself unless you really really like a girl, and don't be a dick. Everything will come together if the interest is mutual.

    I usually try to pay for meals on "dates," and if there is any opposition, I offer to let them pay the next time. Which not only leaves the door open for a next time, but keeps it on a friendly level. I think if you treat girls as friends from the beginning, it gets easier to take it to an emotional level later, or keep things friendly if things don't work out.

    Get your heart broken a few times and you'll be fine.

  9. thegr8brownie says:
    Tue, 24th Feb 20093:48 pm 

    dude,

    nice guys finish last. period.

    look at what Sam and Lauren said for proof.

    stick in there, wait it out, you’ll find your match. the problem is the kind of girl you are looking for needs to be more mature to appreciate you, i say go for older women.

    I’m not going to lie, being a little bit more of an ass would help you, but it would only help find the wrong kind of girl. but I would ditch the flowers and car door openings, they go unappreciated or misinterpreted.

  10. Sarah says:
    Tue, 24th Feb 20094:11 pm 

    please give me a call. i will date you. i’m in a similar situation actually. i do everything right but guys just dont want to put in the effort to make something last. i am thin, white skin with a natural tan, medium length black hair. i go to a good university and am focused on working in the healthcare industry. my # is 415-254-4422.

  11. Amanda says:
    Tue, 24th Feb 20094:12 pm 

    Flowers on a first date? I think I just threw up in my mouth a little. It's a little over the top. Just sayin. Opening car doors is nice though. You are taking her our to dinner, that's enough! Too much can be overwhelming. Also, you don't really sound like the type of guy who just lets it flow. If you click you do, if you don't you don't.

  12. twinkie says:
    Tue, 24th Feb 20094:40 pm 

    too nice= creepy

  13. LKO says:
    Tue, 24th Feb 20095:23 pm 

    Become an asshole.

  14. Caitlin - University says:
    Tue, 24th Feb 20096:01 pm 

    You're the type of guy who is TOO nice and TOO easy to stamp a big "Friend Zone" on. If you're looking for a girlfriend you won't find one…stop looking and eventually, someone will come to you. You're trying to hard to make yourself look good.

  15. HOLY crap... says:
    Tue, 24th Feb 20096:46 pm 

    Did that chick just seriously give her phone number out on an internet blog post????

    WOW.

    I'm sooo hoping that's a joke!

  16. Jenn says:
    Tue, 24th Feb 20096:57 pm 

    quit being a pussy, stop trying to "make all the right moves" girls like it when you ask them out to have a plan, know where you are going. I bet you always ask "Where would you like to eat?" "Where do you want to go" have a plan she will tell you if she doesn't like something. But she will like you more if you are just yourself.

    Advise from http://www.ThePleasureEden.com

  17. holly says:
    Wed, 25th Feb 20098:43 am 

    i'm from the south where the "chivalrous" behavior described are expected and run-of-the mill. doing those things is not a sign a person is an asshole or a "nice guy," but how the individual views himself for doing them is. i'm sure you will be relieved after the "become an asshole" comments to hear that you are in fact already sound like an asshole of the first degree. extra douche points for not mentioning wanting a girl with any sort of similar interests, etc. but just "a" girlfriend… any girlfriend who will give you reinforcement for thinking you've cracked some kind of code to sexy time in exchange for completely uninventive standards of dating chivalry

  18. Kallie says:
    Wed, 25th Feb 200910:04 pm 

    Wow. If I were this guy, I would stop complaining… I’m 20 and I’ve never been in a relationship. yeesh.

  19. Jennifer says:
    Thu, 26th Feb 20097:19 pm 

    i think hes a catch, but he shouldnt have to talk about himself so much if all those things shine through on their own.

  20. Rick James says:
    Fri, 27th Feb 20093:09 pm 

    dude, you find love as soon as you stop looking for it.

    and yea be an asshole. punch a baby, steal some candy, and drink a couple beers.

  21. kylie says:
    Sat, 28th Feb 20092:05 am 

    don't give up being chivalrous – meaning opening doors and getting their coats etc, but flowers? that's way too forward on a first date. keep that for when you mess up or its a special occasion. keep it low maintenance – it won't scare girls off.

  22. very true says:
    Fri, 2nd Mar 20121:53 pm 

    it is the women that have become so very nasty, and certainly have a very bad attitude problem. this is the absolute reason why meeting women is so difficult for us men today. women really do not know how to act, around men. they are too picky, and play very hard too get. you women that are like this, are such losers today. there are plenty of us good men that are not playing games, and would certainly like too meet a good woman to be with. cannot blame men for this.

Tell us what you're thinking...