This week Tia tackles the hard question of whether women should open up their pocketbooks on dates.

Dear Tia,

I’m in my early 30’s and I’m single, but dating. My problem is simple: I have a hard time letting men pay when they take me out. It’s not that I’m dating guys who aren’t professionals or can’t afford to cover the bill. I just feel like I’m at a disadvantage when the gentlemen foots the expense; I don’t want anyone who I’m out with thinking that I owe him something. My girlfriends say I’m tripping. Am I? – Willing to Pay My Way

Dear Pay My Way,

I think you’re both right. In a traditional sense, it’s definitely appropriate to let a man court you. If he asks to take you on a date it is normal to expect him to pay for whatever type of entertainment you undertake that night. However, I also understand your perspective as well. In modern times traditional gender roles aren’t always applicable (especially given the economy), so if you’re uncomfortable about who should pay ask your date – beforehand. During the pre-date conversations get his perspective on what his expectations are and share yours. In addition, I don’t think you should consider going out with anyone who you think would expect “physical compensation” after bankrolling a movie or dinner. Lastly, it’s important to consider a few things before you pull out your cash, especially on the first few dates. Do you always want to go Dutch or pay his way? Do you want to convey the message that you don’t think he can afford to finance your dates? Are you comfortable with the financial dynamic you’re establishing if the relationship moves forward? If the answer to each of these questions is no, keep your hands out of your wallet until you get to know your potential beau a bit better.

Dear Tia,

I’ve been dating this guy that I’ve known for almost 18 months. I’m 19 and he’s 21. We have a lot in common; our birthdays are even one day apart. But he has a lot of drama. After we hung out for a while he told me that he had a baby on the way. Despite that, he called and texted me all the time and that didn’t change even after we became intimate. He told me things - like he wanted us to take a trip together for our birthdays - that made me feel like he planned on being serious. He even called me once while his child’s mother was there and said that he wasn’t dealing with her anymore. I mean, who would say that in front of someone else? One night I told him how I felt about him via text and immediately things started to change. He said if he knew I was going to “catch feelings” he wouldn’t have started messing with me - I spent two hours on my sister’s bathroom floor crying my eyes out. We stopped seeing each other for a while, but that all changed once my sister intervened. She sent him an instant message saying how happy he made me and that he should stop playing. He said he didn’t know why we stopped speaking. I still love him. Should I approach him or wait? – A Teenage Love

Dear Teenage Love,

I say run, quickly. And don’t call him. People can say anything but their actions show you how they truly feel. That boy has game. He didn’t put his child’s mother on “blast” to benefit you, it was to hurt her and make sure she knows she can be replaced – and what he did “for you”, he did to you. His callous behavior when you expressed your feelings is comparable to what he did to his child’s mother. We can’t help who we care about, but we can control what we do. I suggest you write out a list of the 10 top values you want your next boyfriend to have (i.e. loyalty, respect, etc…) and put it over your bed so whenever you’re talking to potential beaus you can size them up according to what you need. Don’t let your emotions and ego get in the way of what’s best for your life plan. I’m sure you have goals to achieve, friends to kick it with and other dudes to date – if not, find all of the above immediately. I implore you to heed my advice… or you’ll likely be this guy’s second – or third – baby’s mama. Don’t do it.

Dear Tia,

I’m 28-years-old. I have been in relationships before but it seems like they never materialize into anything deeper or serious. People just leave my life without any wrong doing from my side. It is either I am too serious, too needy or they found someone else. How do I break this? I want to start my own family soon, but how do I do that when I cannot maintain a relationship. – Ready to Settle Down

Dear Ready,

I completely understand your desire to have a meaningful relationship. It’s natural. It’s healthy. However, I implore you not to let what you want stand in the way of what you need. It seems like you answered your own question in your letter. By asking whether you’re too serious or too needy, you’re acknowledging that even you are spotting these red flags in your behavior. Simply telling you to stop it isn’t enough, so I suggest you look into why you’re feeling the push to make a committed relationship happen. In the big picture, you have a lot of time to find your Mr. Right – even if it doesn’t seem like it. Have faith that there is someone out there just for you. So the big question is what do you do in the “in between time”. Well, it’s a great time to work on you. What’s leading you to pick the men who perpetuate your insecurity? Why are you choosing to pursue serious relationships with men who aren’t interested in being monogamous? What things do you need to work on to attract the kind of man truly want? Do you like and love yourself? Working on these things won’t guarantee that you’ll find a mate as soon as you’d like, but they will ensure that you’re ready for a good man when you meet him.