Widower Wednesday: A Widower with Benefits

Widower Wednesday

Book update: I finished the second and (hopefully) final book galley edits last night. The Ultimate Dating Guide for Widowers is THIS close to being done. Yay!


Whoever sent me the following email didn't leave a valid email address for a reply. So here's the email (edited to take out some personal, identifiable information) and my answer.

A short month ago I took a trip to Chicago to meet with my two best friends for a girls trip. The second night in town we decide to go to the local pub for a few drinks. The bartender brings us a drink and says it's from the guy at the end of the bar. I told her we have to go say thank you. So we did then I ordered him a beer and we all start talking. My friend says that's Ben and that his wife passed away from cancer two months ago. Of course my heart just broke for him right away. We all continued to mingle as a group and had a great night.

The next morning I had a Facebook friend request and am email from Ben. It said it was nice to meet you and hopefully we will see each other again soon. We start chatting and flirting back and forth on FB. He was very honest with me and said that he doesn't know if he is ready to date that he just wants to have fun and that doesn't mean just sex. During this week I am in town he mentions how he enjoys talking to me more than he expected. We continue to talk and flirt a few more days. He asked me out while I was in town to my surprise I really didn't think he was serious so I put it off for a few days. He continued to ask so on my last day in town I went out with him! We stayed up all night talking, kissing, and I had already determined I was not sleeping with him and I let him know that upfront. I was very honest with him and told him I didn't want to be the rebound girl. Hope that wasn't insensitive I am just a very honest person. To my surprise I felt an instant connection with him.

So I come home we continue to talk on the phone and text. A week goes by and we decide were going to be spontaneous and meet halfway.  So we meet and we go out and have a great time together. We do end up sleeping together we have always had not only the emotional connection but the physical connection was just as strong.

Now another couple of weeks have gone by and we talk more on the phone and text several times a day. He has made the initiative for us to meet on next weekend. I'm just confused I know he still has to be grieving. But why would he drive 4 hours to meet me, meet me again next week. Would you drive and make this effort for a friend with benefits?

He tells me how much he likes me but I know he is not ready for anything serious yet which I don't blame him. I'm protective of my feeling and I am taking a chance of getting my heart broke. But how can I treat him different than I would if I was dating anyone else? Would I expect them to know after one month, heck no! Why do I feel the need to know how he feels about me this soon? My friend tells me to stop analyzing and just take it slow and have fun. I'm trying but I feel really guilty if I go on another date with someone else because I know my heart lies with him. How long should I wait for him? I'm patient and not in a hurry but I don't want to be the fool or rebound.

Please help what do you think I should so?




If he says he's not ready for a serious relationship, then take him at his word. He probably enjoys the company and the sex. (And, yes, most men would drive four hours to meet someone if he thought he was going to get sex out of the meeting.)

Before you meet up with him again, you need to decide what it is you want from. If you have feelings for him or think there might be something more to the relationship, then you need to set some different expectations and let him know that you want something more serious. This gives him the opportunity to decide what he wants. Honestly, if he's only been widowed a couple of months, he probably has no idea what he wants other than company. It probably feels good for him to have some female companionship occasionally. Where he's so recently widowed, it might take him several months to really know if he's ready for a serious relationship with you.

If you do want something serious and he says he wants that too, dial things back a bit. He needs time to sort out his feelings. Next time you meet with him hold off on the sex and focus on getting to know him and where he's at a little better. It will give you a better idea of either of you are ready for something more serious.