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Why Won’t She Talk to Me!

August 29th, 2008 | No Comments | Posted in What The Hell?

Dear Bitter Single Guy: I have been seeing this woman for almost a month now. She is a very traditional, quiet woman. She rarely ever calls, and I am the one who sets up all of the dates. The dates have been fun, but she has not opened up to me. I guess I just feel like I’m doing all of the work here, which was cool for the a few weeks, but now it’s becoming a problem for 2 reasons: 1) It’s hard for me to get close to someone who does not let me know how they feel. 2) I really don’t wanna waste time here. How do I handle this? Do I open up a little more, which triggers her opening up more? Or, ask her how she feels about everything? Please help. I truly like this girl, but feel like we’ve been in limbo. ~Dating a Closed Book~

Dear DCB: The Bitter Single Guy wants all his readers to pay attention to your letter. There are those folks out there who believe that it will always be a woman wishing that a man were more forthcoming with his feelings.  Your example DCB, enlightened relationship-focused man that you are, shows that we’re all a little more alike than we are different.

DCB, the BSG thinks that a month really isn’t long enough to decide that you’re wasting your time in this relationship.  The BSG has a jar of mayonnaise that’s significantly older than your relationship. (and oddly, the mayonnaise also doesn’t talk about what IT wants.  Hmmm.) Give your Reluctant Rose a little time to warm up to you.  It also couldn’t hurt to continue to encourage her to share. The BSG recommends asking her about fun things in her childhood; that should be a relatively safely intimate conversation.

For the ownership of the dating ‘vehicle’ if you will (the calling, the organizing dates, etc.) the BSG recommends a straightforward, staged approach.  You should schedule the next date, but let her know that the activity gets to be whatever she wants. If Reluctant Rose isn’t used to being the organizer, it may take her a few tries to get the hang of this. 

Overall, the BSG doesn’t recommend pulling the plug until at least the three-month mark if you’re still not getting anything.  But it’s the BSG’s guess that Reluctant Rose doesn’t even know that these are needs of yours…tell her, for heaven’s sake.

Caught Between the Devil and The Deep Blue Sea

August 28th, 2008 | No Comments | Posted in I'm A Tool

Dear Bitter Single Guy: I have been with someone kinda for the past year and a half. I say kinda because he travels all the time and i see him maybe once in 3 months and sometimes longer. At first I was ok with this but eventually i got tired of playing second fiddle to his job so I started trying to talk to him about it; for over 8 months without success. He wasn’t there for me when both my parents died, he never calls me at Christmas or on my birthday and he always refuses to take me out. Inevitably I have met someone else who loves me and cares for me deeply. Someone who appreciates me and I can almost call my soul mate. I was getting ready to dump the other guy when he came around finally and was ready to talk about things but while my feelings for him are no longer the same, it still exists to some extent and now i am caught between the two of them. I know it seems kind of obvious what to do but i am still apprehensive and scared for some reason i can’t explain. What do i do? ~Between a Rock and a Hard Place~

Dear BRHP: The Bitter Single Guy and you both know that this is easy. Dump the guy you’ve ‘kinda’ been with. You know him, right? The one who doesn’t call you on your birthday or holidays, the one who doesn’t take you out, the one you only see every few months, the one who wasn’t supportive of you when your parents died (really, BRHP?).  That one, right? Dump his sorry ass. You’ve been a doormat for him long enough. (The BSG feels strongly about basic participation in a relationship, as you can see.).  You’d be better off alone, but instead of being alone, you’ve found a nice guy! You’re done. ~BSG~

Craving the Unavailable

August 28th, 2008 | No Comments | Posted in I'm A Tool

Dear Bitter Single Guy: So, there is this girl who I met during a summer program at UCSF. She says she has a boyfriend, but doesn’t really defend him. We got really close really fast; going to all these different places around San Francisco to eat and have fun. After we both went back to our respective universities (she is in Chicago, I’m at Baltimore), we talk online and on the phone a lot. She tells me almost all the stories of her life and I do the same with mine. I really really like this girl but since she has a boyfriend, I don’t think I can really tell her how I feel. Long Distance Longing

Dear LDL: The Bitter Single Guy is SUCH a fan of summer romance!  Oh how his memory goes back to those times…wait…nope; the BSG never had a summer romance. Damn.

LDL this delicate flower is taking the age-old path of warming up to someone who is completely unavailable.  She knows, even if you don’t, that she can safely hang out and get close to you with no fear of interrupting her life or her current relationship.  Enjoy your summer for what it was, keep warm memories of your Delicate Flower, and meet a girl in Baltimore who similarly makes your toes curl.


The Minefield of Love

August 25th, 2008 | 1 Comment | Posted in Stay Or Go?

Dear Bitter Single Guy: I recently had a pen pal who was in jail. We carried this on for well over a year. I picked her up a couple of times when she had a furlough. We kissed a lot, but nothing more. She has to live with her parents for now and her father doesn’t want her to date. I’ve been picking her up from work for lunch almost every weekend because I travel for work. She doesn’t want to go against her father because she is thankful for his help and he has a problem controlling his temper. He knows about me but won’t meet me yet. She is also in a 12 step program. She also has debts and other baggage to sort out. She says she feels guilty because she can’t offer anything but these lunch dates for now. She also says she doesn’t know if there’s a future for us.


I don’t know either, but I feel like after all of the writing back and forth and the help I’ve given it’s worth a shot. I’m not sure how long I should wait and keep working on her. I can’t help but think that if she wanted to end it she wouldn’t keep calling and texting. She calls almost everyday and says have a good day or I’m thinking of you. I want us to try when her mind is clearer. So my question is how long should I keep trying to win her over? I Just Keep Trying


Dear IJKT: The Bitter Single Guy is freaking out a little on your behalf!  Let’s catalog this issues here together, shall we?

  • Your Tantalizing Tulip is just out of jail and re-adjusting to her non-incarcerated life.
  • She lives with her hot-tempered father who doesn’t want her to date.
  • She’s in a 12 step program (which also doesn’t want her to date for the first year).
  • She’s managing financial problems.
  • She’s feeling guilty because she doesn’t have more to offer YOU.

Does the BSG have the list right, IJKT? Is this actually the woman that you’ve decided to pursue romantically? IJKT, the BSG probably isn’t the guy you should have come to.  You wonder how long you should try to keep winning her over? You’re way past due, IJKT. There is nothing but heartbreak for you AND for Tantalizing Tulip here.  Because she calls and texts you and tells you she’s been thinking of you is NO reason to enter this mine field. This Tantalizing Tulip is probably working her butt off to reclaim her life from some bad decisions and guilt at not meeting YOUR needs is only going to push her toward the edge. Check out the rates of recidivism for your Tantalizing Tulip and realize what an uphill battle she has.


Do yourself and Tantalizing Tulip a favor and step back…WAY back…until she’s gotten her world back under some control and don’t let your ‘investment’ in this girl become a reason to keep pursuing her.


Cryptic Messages and Cuddling

August 21st, 2008 | No Comments | Posted in I'm A Tool

Dear Bitter Single Guy: Here is what happened… I’ve known this girl for a while, not really attracted to her until that night but up to it nothing really there. So one night we were hanging w/ a group of friends at the resort we go to and one of our other friends (a good friend of mine) isn’t leaving her alone after she told him that she does not like him… anyhow she asks me to pretend we are together for the night.  i go along w/ it and that night we do have fun, dance the night away whispering in each other’s ears laughing the whole night… even after this guys left to go home… as we are walking back to our respective rooms (they are next to each other) I ask her to come in and hang out since a few of our friends were still up and watching TV in my room.. .she does… sits next to me and we cuddle… then our friends leave and we move on to the bed to warm up because it was freezing that night… and as were just holding each other.. I kissed her.  After the initial kiss we made out for a bit then fell asleep in each other’s arms. Didn’t go farther than that. For like 2-3 weeks after we’d talk on the phone for like an hour and a half to 2 hrs a night… I’ve seen her 2x since and it’s a little weird and our phone calls have gotten less frequent and shorter. This weekend I’m going to see her again as we’re going to the beach w/ friends?  I do like this girl but am completely oblivious to female signs etc…  Can you help me, BSG? ~Lost in The Fog

Dear LITF: The Bitter Single Guy is slightly incredulous.  DudeBro, do you and your friends really hang out at a “resort” where you have private rooms and get to cuddle and make out? Is this an ad for the recycled version of Beverly Hills 90210? Dude, the BSG hung out at a rockpit when he was a young impressionable teen.  (For those of you unaware, a rockpit is just like a lake without grass, trees, fish, or other wildlife.  Construction crews dig deep holes to use the dirt somewhere else and they dig deep enough that the hole fills up with water. Voila. Rockpit).

OK, the weird setting aside, the BSG understands that reading the cryptic messages of the opposite sex is frustrating.  Notice that the BSG says ‘opposite sex’ and not ‘women’. That’s because the BSG gets just as many letters from women trying to interpret the vague messages from men as the other way.

LITF the answer is what you think it is. Talk to her. Tell her what you want. Find out what she wants. Decide what you want together (if anything). Lather. Rinse. Repeat.


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