Steve Mazzuchi is the managing editor at Mademan.com. Steve’s written about dating for Men’s Health, Men’s Journal, Maxim, ESPN The Magazine and Esquire. We gave Steve 5 questions about love and money and he answered them.

1. Ok, so the date is not going so well and we both know it.  Then the bill comes. Do I still pay? Typically, as a guy, I’d pay but I’m not seeing any return on my investment.

Steve says: Yes, for multiple reasons. First, it’s the gentlemanly thing to do. Second, if you saw Zoosk’s latest survey, you know you don’t have to spend a lot on a first date. And third, it never hurts to make a positive impression. Girls talk, and you want this one saying only pleasant things to her friends because you never know, one of them could be your dream girl. Talk about a return on your investment!

2. Online group deal coupons are my latest addictions, but I hate to look like a cheapskate!  Is it cool for me to use these deals on dates or is that setting me up for failure?

Steve says: In a word, nope! It’s tempting, yes, but no girl wants to feel like you got a “deal” on your date with her, and research shows the majority will be turned off. Now, if you’ve been together a while and have a higher comfort level together, that’s a different story, but as a general rule, no coupons on the first date. Capeesh?

3. When a date offers to go Dutch, I usually decline, but sometimes she insists and it can get kind of awkward. Should I really put my foot down and pay for 100% [OF?] the date?

Steve says: If you ever want to see this girl again, you should pay. It sends the message that you are serious and this is, in fact, an actual date (as opposed to a one-way ticket to the friend zone). If it starts to get awkward, say something like “you can get the drinks at our next stop.” This not only moves things along, it sets up the next phase of the date and lets her know you’re into her. And when she does actually pick up those drinks, you’ll know she is into you too.

4. I have been dating a guy for 2 months and he recently asked me out on a date that far exceeds my own budget.  Do I need to be upfront that I can’t afford it, or should I assume he is going to pay since it was his idea?

Steve says: Ah, that’s a tricky one, but two months is enough time for you to feel comfortable being upfront. The key is timing. You want to wait for a moment when you are out together, having a good time and feeling close, to share your feelings about the situation. A standup guy will understand, and from there you can figure out the best course of action. Which is undoubtedly preferable to you getting stuck with a very uncomfortable bill.

5. My boyfriend whom I’ve been dating for six months makes a lot less money than I do. At first this was not a problem, but now it seems like I am paying for everything. We really like each other but am I being taken advantage of?

Steve says: You’re not being taken advantage of—intentionally, anyway. But you have to ask yourself a couple questions. 1) “Is he bringing something to the table that makes up for his lack of income?” And 2) “Is this how it’s always going to be, or is it temporary?” Case in point: one of my friend’s then-boyfriend made less than her when they met, but he was 1) a fun, charming guy who happened to be a fantastic cook and 2) in grad school studying computer science. So she could answer “yes” to both questions and, years later, they’re happily married. Of course, if you find yourself answering “no” to both questions, you’ll need to have some sort of talk—or be prepared to spend a lot of nights staying home watching TV.

Want some ideas for wallet-friendly summer dates? Check out Steve’s suggestions here!

Photo via Flickr. Creative Commons Attribution License.