The Bitter Single Guy’s Relationship Advice

The Minefield of Love

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.

~BSG~