Q & A / Is He Just Cheap or Flat Broke?

Q: Hi, Chris:

I've recently been on two stellar dates with a man I met online. The second date ended in a memorable kiss. He has many of the qualities I'm looking for in a potential partner and I am very interested to learn more about him... except that I am concerned by a potential red flag: on neither date did he offer to pay.

The first date, I let it slide, as we just met for coffee. However, I was very surprised when, on our second date, he didn't stop me when I pulled out my wallet. After dinner, we went out for one more drink at another spot, and he didn't offer to pay there, either!

By no means am I a gold digger... and once it gets going, I actually appreciate a relationship that has some balance among partners. However, I'm still a little old-fashioned when it comes to the early stages of dating and am concerned about what his unwillingness to foot the bill might mean--either about his interest in me or about his attitudes about money in general.

If the man doesn't offer to pay... is this a red flag or, worse, a deal breaker?

--- Feeling used and confused in Buffalo, NY

A: Dear Bachelorette:

Two stellar dates? He sounds stellar cheap to me.

Huge red flags are flying here and everywhere!

Yes, the man should always pay on the first date--and in my opinion, the 2nd and 3rd, too. Although I'm with you at some point the woman should step up to the plate (such as offer to pay by the third or fourth date, but never the first few!)

And for those guys who ALWAYS like to pay (bless you), the woman should generously reciprocate with either home-cooked meals here and there, tickets to a concert, take him to HIS favorite restaurant, etc. No man ever wants to feel used, but there are still men out there who enjoy playing the role of "protector and provider." And when a woman takes care of her man, too (once you're past the initial dating stage), the whole world is a happier place :)

I'm sure guys and girls in their 20's will dispute what I say, but you're in your early 30's...and that's about where the cut-off seems to be these days. Women 30's and older pretty much expect a man pay on a first date. Let twenty-something's do their own thing (okay, I still think a guy should pay the first couple dates, no matter how old or not.)

You seem enchanted with this fellow (and good men are hard to come by), but keep your wallet tightly tucked in your purse next time! In fact, why were you so quick to draw it out for coffee, dinner AND drinks?

The whole coffee things bothers me almost more than he not buying dinner (okay, they're both in poor taste)....but if the guy can't offer to pick up coffee, geez! The only exception is if he arrives super early and already bought his latte. Even then he should still offer to buy yours (it's what gentlemen do!)

I'll nix your theory maybe he's not interested (assuming after your coffee date he's the one who asked you out for dinner.) A guy doesn't ask you on a second date if he doesn't like you, especially since he didn't even pop for coffee first time around.

Because you really like this guy, go ahead and explore things further---but under no circumstances are you to pay the next couple dates. I don't care if that means you have a face-off or get up and go to the bathroom when the check arrives (good idea in his case!)

One other thing---are you sure this guy is really employed?

It could be he's out-of-work and truly flat broke. In this scenario, do you really want to continue dating someone who needs to get his act together? The last thing you want to do is fall for any, "I'm a victim of the economy and broke" act. If this turns out to be the case, he is in no position to date anyone until he has an income.

If you know for a fact he really is gainfully employed, then please follow my earlier instructions. The truth will come out within the next few dates.

Your intuition is RIGHT ON, so continue to trust it. If you let him take advantage of your generous spirit again, then "tsk tsk" on you (but I know you won't let that happen :)

Happy eating--on his dime next time. And the next.

P.S. I like your generosity, though...but use it on a new guy you DON'T like. In other words, if you ever go on a first date and you absolutely know you don't want to see the person again (yet sense he's really digging you), I give you permission to pay up. I've done it myself a few times, out of guilt :)

Q & A / Weekend Lover Not Enough For Her

Q: Hi, Chris:

I've been dating a wonderful guy for about 1.5 years now.

We met on a dating website and hit it off immediately. Both of us are divorced with kids, and our families have grown to love each other dearly! My kids are in college, and his two kids are in high school (one is going to college this fall.)

He knows I want to get married, but he is still dealing with issues. How long should I wait?

I certainly don't want to give him an ultimatum, but I also want to get on with my life. I'm going to be 50 soon (he's 48); I don't want to waste my time if he's not interested in marrying me. And if he is thinking of waiting for both kids to be in college, I'm not sure I want to wait four years.

We are together all weekend, but when school starts on Monday, he is back to being a full-time dad and only has time to talk to me by phone.

I really do love him. He is the total opposite of my ex-husband. He is a real gem, but I don't know what I should do or say.

Help.

--- Frustrated in Ft. Lauderdale

A. Dear Bachelorette:

I hate to say this (and experienced it once myself); BUT, his kids come first and foremost--get used to it, or get out.

Since I don't see you "getting out," then deal with the fact he's a father first, and your lover/friend second. Personally, I think it shouldn't be a contest (ever!), but as someone who doesn't have children, it's easier for me to take this stance.

I think the real issue here is lack of communication. You've been with this man for almost two years, so you're way overdue for THE TALK.

Make him a lovely, romantic dinner and afterward take a stroll outside. Hand-in-hand, you can easily (and gently) tell him how you feel, and if he loves you as much as you love him, then he should take what you say very seriously. You have the right to know if this man plans on marrying you, and if so WHEN.

It sounds like you're his weekend lover. He shuts you out during the week (except for phone calls), when he turns into playing the role of Mr. Mom. While I commend his fatherly duties, it seems a little out-of-whack to me. Personally, if this man is crazy about you, he should sneak an evening or two during the work week. Even a quick bite to eat mid-week (with kids in tow or not) would be nice.

It sounds like a long-term relationship of convenience for him. Now go find out how much love there is in his tank (enough to marry you when you turn 50?) That actually would be pretty cool to celebrate both lasting love and your birthday!

While you don't want to give him an ultimatum, please be very clear about your needs. If he's not going to start planning marriage with you (and yes, 4-years is too long to wait, if it's going to make you miserable), then perhaps this isn't the right relationship for you.

You're not playing games here--this is serious business. And kids or not, YOU should be at the top of his list too!

I hope he steps up to the commitment plate. Let me know.